Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element having a cathode, an anode, and one or more organic layers disposed between the cathode and the anode; at least one of the one or more organic layers contains a first component and a second component; the first component is a compound represented by formula (1), and the second component is selected from the group consisting of an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an alkali metal-containing organometallic complex, an alkaline earth metal-containing organometallic complex, and a rare earth metal-containing organometallic complex.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic electroluminescent element and an electronic device. BACKGROUND

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter, also referred to as an organic EL element), holes are injected from an anode, and electrons are injected from a cathode, into a light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] The element performance of conventional organic EL elements is not sufficient. In order to improve the element performance, improvements in organic EL elements have been gradually made, but further higher performance is required.

[0004] Patent Document 1 discloses the use of a compound having a specific structure in an electron transport layer of an organic EL element.

[0005] PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent Document 1: Chinese Patent Application Publication No. 114122299. SUMMARY

[0006] An object of the present application is to provide an organic EL element with higher performance.

[0007] The present inventors have intensively studied in order to achieve the above object, and as a result, have found that an organic EL element with a low driving voltage and high efficiency in a range from a low current density to a high current density can be obtained by using two specific components in combination in at least one layer of an organic layer of an organic EL element, and thus have completed the present application.

[0008] In addition, the present inventors have intensively studied in order to achieve the above object, and as a result, have found that an organic EL element with a low driving voltage and high efficiency even at a low current density can be obtained by using two specific components in combination in at least one layer of an organic layer of an organic EL element, and thus have completed the present application.

[0009] According to the present application, the following organic EL element and the like are provided.

[0010] 1. An organic electroluminescent element comprising: a cathode, an anode, and one or two or more organic layers disposed between the cathode and the anode; at least one of the one or two or more organic layers contains a first component and a second component, the first component is a compound represented by the following formula (1), The aforementioned second component is selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, organic metal complexes containing alkali metals, organic metal complexes containing alkaline earth metals, and organic metal complexes containing rare earth metals; [Chemical Formula 1] In formula (1), R1 to R 10 at least one of which is a group represented by formula (1A); R1 to R 10 which is not the group represented by the aforementioned formula (1A), is a hydrogen atom or a substituent A; wherein R1 to R 10 at least three of which are each independently a group represented by the aforementioned formula (1A), a substituent A, or a hydrogen atom which is a deuterium atom; In formula (1A), L 1A is: a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 2-valent heterocyclic group having 5 to 50 ring-forming atoms; n1A is an integer of 0 to 3; when n1A is 0, (L 1A ) n1A is a single bond; when n1A is 2 or 3, a plurality of L 1A are connected in series with each other, and the structure within the parentheses is bonded to the L 1A which is farthest from the anthracene skeleton; and a plurality of L 1A may be the same or different; X 11A is C(R 21A )(R 22A ), N(R 23A ), O, or S; one group or more consisting of 2 or more adjacent ones of R 11A to R 18A is bonded to each other to form a substituted or unsubstituted monocyclic ring, or is bonded to each other to form a substituted or unsubstituted fused ring, or does not form the aforementioned ring; when the aforementioned substituted or unsubstituted monocyclic ring is formed, one of the atoms constituting the monocyclic ring is bonded to L 1A , or one of R 11A to R 18A and R 21A to R 23A not participating in the formation of the monocyclic ring represents a bond to L 1A ; When forming the above-mentioned substituted or unsubstituted fused ring, one of the atoms constituting the fused ring and L 1A R that is bonded to or does not participate in the formation of the fused ring 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A Key; When the aforementioned monocyclic ring and condensed ring are not formed, R 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A Keys; Does not indicate the same as the above L 1A and does not form the aforementioned ring R 11A ~R 18A and R 21A ~R 23A are each independently a hydrogen atom or a substituent A; When there are two or more groups represented by formula (1A), the two or more groups represented by formula (1A) may be the same as or different from each other; The substituent A is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 Each independently is: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; When there are two or more substituents A, the two or more substituents A may be the same or different from each other; R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same as or different from each other; The compound represented by the aforementioned formula (1) does not contain the structure represented by the following formula (M1), the structure represented by the following formula (M2), the structure represented by the following formula (M3), and the structure represented by the following formula (M4) in the molecule; [Chemistry 2] .

[0011] 2. An organic electroluminescent element comprising: cathode, Anode, and One or more organic layers disposed between the cathode and the anode; At least one of the one or more organic layers comprises a first component and a second component, The first component is a compound that satisfies the following formula (R1) and formula (R2), and does not contain the structures represented by the following formulas (M1) to (M4) in the molecule. The second component is selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, organometallic complexes containing alkali metals, organometallic complexes containing alkaline earth metals, and organometallic complexes containing rare earth metals; [Chemistry 3] In formula (R1), GSP_slope represents the giant surface potential gradient; in formula (R2), LUMO represents the energy level of the lowest unoccupied orbital.

[0012] 3. An electronic device comprising the organic electroluminescent element according to 1 or 2 above.

[0013] 4. A compound represented by the following formula (2), [Chemistry 4] In formula (2), Ring a is: a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 6 to 50 ring-forming atoms; R 101 ~R 107 , R 111 ~R 113 , R 121 ~R 125 , and R 131 ~R 135 each independently represents a hydrogen atom or a substituent R; wherein at least one of R 111 ~R 113 is a substituent R, or the aforementioned ring a has at least one substituent; the substituent R is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 ~R 907 each independently represents: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 ~R 907 when two or more are present, two or more of R 901 ~R 907 may be the same or different; When two or more substituents R are present, the two or more substituents R can be the same or different.

[0014] According to the present application, an organic EL element with higher performance can be provided. BRIEF DESCRIPTION OF DRAWINGS

[0015] Figure 1 FIG. 1 is a diagram showing the schematic configuration of an organic EL element according to one embodiment of the present application. DETAILED DESCRIPTION

[0016] [DEFINITIONS] In the present specification, hydrogen atoms include isotopes different in the number of neutrons, i.e., protium, deuterium, and tritium.

[0017] In the present specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom, is bonded to a position capable of being bonded, which is not indicated by a symbol such as "R" or "D" indicating a deuterium atom.

[0018] In the present specification, the number of ring-constituting carbon atoms represents the number of carbon atoms among atoms constituting a ring of a compound (e.g., a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound) in which the atoms are combined in a ring shape. When the ring is substituted with a substituent, carbon included in the substituent is not included in the number of ring-constituting carbon atoms. The "number of ring-constituting carbon atoms" described below is also the same unless otherwise specified. For example, the number of ring-constituting carbon atoms of a benzene ring is 6, the number of ring-constituting carbon atoms of a naphthalene ring is 10, the number of ring-constituting carbon atoms of a pyridine ring is 5, and the number of ring-constituting carbon atoms of a furan ring is 4. In addition, for example, the number of ring-constituting carbon atoms of a 9,9-diphenylfluorene group is 13, and the number of ring-constituting carbon atoms of a 9,9'-spirobifluorene group is 25.

[0019] In addition, when an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-constituting carbon atoms of the benzene ring. Thus, the number of ring-constituting carbon atoms of a benzene ring substituted with an alkyl group is 6. In addition, when an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-constituting carbon atoms of the naphthalene ring. Thus, the number of ring-constituting carbon atoms of a naphthalene ring substituted with an alkyl group is 10.

[0020] In the present specification, the number of ring-forming atoms represents the number of atoms constituting a ring itself in a compound having a structure (e.g., a monocyclic ring, a fused ring, and a ring assembly) in which atoms are combined to form a ring (e.g., a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Atoms not constituting a ring (e.g., a hydrogen atom that terminates a bond constituting a ring), and atoms contained in a substituent when the ring is substituted with the substituent are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of ring-forming atoms in a pyridine ring to which a hydrogen atom is bonded, or the number of atoms constituting a substituent is not included in the number of ring-forming atoms in a pyridine ring. Therefore, the number of ring-forming atoms in a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. In addition, for example, the number of ring-forming atoms in a quinoline ring to which a hydrogen atom bonded to a carbon atom of the quinoline ring, or an atom constituting a substituent is not included in the number of ring-forming atoms in a quinoline ring. Therefore, the number of ring-forming atoms in a quinoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0021] In the present specification, "carbon number XX to YY of a ZZ group, which is substituted or unsubstituted" in the expression represents the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of a substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0022] In the present specification, "carbon number XX to YY of a ZZ group, which is substituted or unsubstituted" in the expression represents the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of a substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0023] In the present specification, an unsubstituted ZZ group represents a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group", and a substituted ZZ group represents a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group".

[0024] In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0025] In addition, in the present specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group is replaced with a substituent. "Substituted" in the case of "BB group substituted with AA group" also means the same, that one or more hydrogen atoms in the BB group is replaced with the AA group.

[0026] "Substituent group described in the present specification" Hereinafter, the substituent group described in the present specification is explained.

[0027] The number of ring-forming carbon atoms of "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0028] The number of ring-forming atoms of "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0029] The number of carbon atoms of "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0030] The number of carbon atoms of "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0031] The number of carbon atoms of "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0032] The number of ring-forming carbon atoms of "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in the present specification.

[0033] The number of ring-forming carbon atoms of "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0034] The number of ring-forming atoms of "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0035] The number of carbon atoms of "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0036] "Substituted or unsubstituted aryl group" As specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in the present specification, the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) and the like can be given. (Here, the unsubstituted aryl group means the case where the "substituted or unsubstituted aryl group" is "unsubstituted aryl group", and the substituted aryl group means the case where the "substituted or unsubstituted aryl group" is "substituted aryl group".) In the present specification, the "aryl group" alone is mentioned, and both the "unsubstituted aryl group" and the "substituted aryl group" are included.

[0037] The "substituted aryl group" means that one or more hydrogen atoms of the "unsubstituted aryl group" is replaced with a substituent. As the "substituted aryl group", for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A is replaced with a substituent, and examples of the substituted aryl group of the following specific example group G1B and the like can be given. Note that the examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are only one example, and the "substituted aryl group" described in the present specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted aryl group" of the following specific example group G1B is further replaced with a substituent.

[0038] ・Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, phenanthryl group, benzo-phenanthryl group, phenalenyl group, pyrenyl group, fluorenyl group, benzo-fluorenyl group, triphenylyl group, benzo-triphenylyl group, tetracenyl group, acenaphthenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, benzofluorenyl group, dibenzo-fluorenyl group, fluoranthene group, benzofluoranthene group, perylene group, and a monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0039] [Chemical Formula 5] [Chemical Formula 6] • Substituted aryl group (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, p-xyllyl group, m-xyllyl group, o-xyllyl group, p-isopropylphenyl group, m-isopropylphenyl group, o-isopropylphenyl group, p-tert-butylphenyl group, m-tert-butylphenyl group, o-tert-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-tert-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and a group in which one or more hydrogen atoms of the monovalent group derived from the ring structure represented by the aforementioned general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0040] • "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in the present specification is a cyclic group having at least one heteroatom in the ring-forming atom. As specific examples of the heteroatom, a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom can be given.

[0041] The "heterocyclic group" described in the present specification is a monocyclic group or a fused ring group.

[0042] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0043] As specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification, the following unsubstituted heterocyclic groups (specific example group G2A), and substituted heterocyclic groups (specific example group G2B), and the like can be given. (Herein, the unsubstituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In the present specification, when only "heterocyclic group" is mentioned, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

[0044] The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" is replaced with a substituent. Specific examples of the "substituted heterocyclic group" can be given as a group in which a hydrogen atom of the "unsubstituted heterocyclic group" of the following specific example group G2A is replaced, and examples of the substituted heterocyclic group of the following specific example group G2B, and the like. Note that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are only one example, and the "substituted heterocyclic group" described in the present specification includes a group in which a hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B is further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B is further replaced with a substituent.

[0045] The specific example group G2A includes, for example, unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0046] Specific example group G2B includes, for example, a substituted heterocyclic group having a nitrogen atom (specific example group G2B1), a substituted heterocyclic group having an oxygen atom (specific example group G2B2), a substituted heterocyclic group having a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) is replaced with a substituent (specific example group G2B4).

[0047] • an unsubstituted heterocyclic group having a nitrogen atom (specific example group G2A1): pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinoxazinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenoxazinyl, carbazolyl, benzocarbazolyl, morpholino, phenoxazinyl, phenothiazinyl, azacarbazolyl, and diazacarbazolyl.

[0048] • an unsubstituted heterocyclic group having an oxygen atom (specific example group G2A2): furanyl, oxazolyl, isoxazolyl, oxadiazolyl, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

[0049] • Unsubstituted heterocyclic group containing sulfur atom (specific example group G2A3): thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, naphthobenzothienyl group, benzothiazolyl group, benzisothiazolyl group, phenothiazinyl group, dinaphthothiophenyl group, azadibenzothienyl group, diazadibenzothienyl group, azanaphthobenzothienyl group, and diazanaphthobenzothienyl group.

[0050] • Monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by General Formulae (TEMP-16) to (TEMP-33) below (specific example group G2A4): [Chemical Formula 7] [Chemical Formula 8] .

[0051] In the aforementioned general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. Among them, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH.

[0052] In the aforementioned general formulae (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the aforementioned general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0053] • Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylquinazolinyl group.

[0054] • Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a tert-butyl-dibenzofuranyl group, and a monovalent residue of spiro [9H-xanthene-9, 9'-[9H] fluorene].

[0055] • Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a tert-butyl-dibenzothiophenyl group, and a monovalent residue of spiro [9H-thioxanthene-9, 9'-[9H] fluorene].

[0056] • a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the aforementioned general formula (TEMP-16) to (TEMP-33) is replaced with a substituent (specific example group G2B4): The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring- forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least either of X A and Y A is NH, and a hydrogen atom of a methylene group when one of X A and Y A is CH2.

[0057] • "substituted or unsubstituted alkyl group" As specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in the present specification, the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B) can be given. (Herein, the unsubstituted alkyl group means a case where the "substituted or unsubstituted alkyl group" is the "unsubstituted alkyl group", and the substituted alkyl group means a case where the "substituted or unsubstituted alkyl group" is the "substituted alkyl group".) Hereinafter, when merely referring to "alkyl group", both the "unsubstituted alkyl group" and the "substituted alkyl group" are included.

[0058] The "substituted alkyl group" means a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" is replaced with a substituent. As specific examples of the "substituted alkyl group", a group in which one or more hydrogen atoms of the "unsubstituted alkyl group" (specific example group G3A) described below is replaced with a substituent, and examples of the substituted alkyl group (specific example group G3B), and the like can be given. In the present specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight chain "unsubstituted alkyl group" and a branched chain "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in the present specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of the specific example group G3B is further replaced with a substituent.

[0059] • unsubstituted alkyl group (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl group.

[0060] • Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, trifluoromethyl group.

[0061] • "Substituted or unsubstituted alkenyl group" As specific examples of the "substituted or unsubstituted alkenyl group" recited in the present specification (specific example group G4), the following unsubstituted alkenyl groups (specific example group G4A), and substituted alkenyl groups (specific example group G4B), and the like can be given. (Here, the unsubstituted alkenyl group refers to a case where the "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and the substituted alkenyl group refers to a case where the "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In the present specification, a mere reference to "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0062] The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced with a substituent. As specific examples of the "substituted alkenyl group", examples of the "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the substituted alkenyl groups (specific example group G4B) can be given. Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" recited in the present specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkenyl group" of specific example group G4B is further replaced with a substituent.

[0063] • Unsubstituted alkenyl groups (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0064] • Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0065] • "Substituted or unsubstituted alkynyl group" As specific examples of the "substituted or unsubstituted aryl group" recited in the present specification (specific example group G4), the following unsubstituted aryl groups (specific example group G4A) and the like can be given. (Here, the unsubstituted aryl group means the case where the "substituted or unsubstituted aryl group" is "unsubstituted aryl group".) Hereinafter, the "aryl group" alone means both the "unsubstituted aryl group" and the "substituted aryl group".

[0066] The "substituted aryl group" means a group in which one or more hydrogen atoms in the "unsubstituted aryl group" are replaced with a substituent. As specific examples of the "substituted aryl group", a group in which one or more hydrogen atoms in the "unsubstituted aryl group" (specific example group G4A) described below are replaced with a substituent, and the like can be given.

[0067] ・Unsubstituted aryl group (specific example group G4A): phenyl group, ・"Substituted or unsubstituted heteroaromatic group" As specific examples of the "substituted or unsubstituted heteroaromatic group" recited in the present specification (specific example group G7), the following unsubstituted heteroaromatic groups (specific example group G7A) and the like can be given. (Here, the unsubstituted heteroaromatic group means the case where the "substituted or unsubstituted heteroaromatic group" is "unsubstituted heteroaromatic group".) Hereinafter, the "heteroaromatic group" alone means both the "unsubstituted heteroaromatic group" and the "substituted heteroaromatic group".

[0068] The "substituted heteroaromatic group" means a group in which one or more hydrogen atoms in the "unsubstituted heteroaromatic group" are replaced with a substituent. As specific examples of the "substituted heteroaromatic group", a group in which one or more hydrogen atoms in the "unsubstituted heteroaromatic group" (specific example group G7A) described below are replaced with a substituent, and the like can be given.

[0069] ・Unsubstituted heteroaromatic group (specific example group G7A): pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, and 1-norbornyl group, and 2-norbornyl group.

[0070] • Substituted cycloalkyl group (specific example group G6B): 4-methylcyclohexyl group.

[0071] • "a group represented by -Si(R 901 )(R 902 )(R 903 ) shown in the present specification" Specific examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) shown in the present specification can be mentioned: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6).

[0072] Here, G1 is "substituted or unsubstituted aryl group" described in the specific example group G1.

[0073] G2 is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0074] G3 is "substituted or unsubstituted alkyl group" described in the specific example group G3.

[0075] G6 is "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0076] The plurality of G1 in -Si(G1)(G1)(G1) are the same or different from each other.

[0077] The plurality of G2 in -Si(G1)(G2)(G2) are the same or different from each other.

[0078] The plurality of G1 in -Si(G1)(G1)(G2) are the same or different from each other.

[0079] The plurality of G2 in -Si(G2)(G2)(G2) are the same or different from each other.

[0080] The plurality of G3 in -Si(G3)(G3)(G3) are the same or different from each other.

[0081] a plurality of G6's in -Si(G6)(G6)(G6) are the same or different from each other.

[0082] • a group represented by -O-(R 904 ) As a specific example (specific example group G8) of the group represented by -O-(R 904 ) in the present specification, the following can be given: -O(G1), -O(G2), -O(G3), and -O(G6).

[0083] Here, G1 is "substituted or unsubstituted aryl" described in the specific example group G1.

[0084] G2 is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0085] G3 is "substituted or unsubstituted alkyl" described in the specific example group G3.

[0086] G6 is "substituted or unsubstituted cycloalkyl" described in the specific example group G6.

[0087] • a group represented by -S-(R 905 ) As a specific example (specific example group G9) of the group represented by -S-(R 905 ) in the present specification, the following can be given: -S(G1), -S(G2), -S(G3), and -S(G6).

[0088] Here, G1 is "substituted or unsubstituted aryl" described in the specific example group G1.

[0089] G2 is "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0090] G3 is "substituted or unsubstituted alkyl" described in the specific example group G3.

[0091] G6 is "substituted or unsubstituted cycloalkyl" described in the specific example group G6.

[0092] • a group represented by -N(R 906 )(R 907 ) As a specific example (specific example group G10) of the group represented by -N(R 906 )(R 907Specific examples of the group represented by -N(G1)(G1) (specific example group G10) include: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6).

[0093] Here, G1 is "substituted or unsubstituted aryl" described in specific example group G1.

[0094] G2 is "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0095] G3 is "substituted or unsubstituted alkyl" described in specific example group G3.

[0096] G6 is "substituted or unsubstituted cycloalkyl" described in specific example group G6.

[0097] The plurality of G1 in -N(G1)(G1) are the same or different from each other.

[0098] The plurality of G2 in -N(G2)(G2) are the same or different from each other.

[0099] The plurality of G3 in -N(G3)(G3) are the same or different from each other.

[0100] The plurality of G6 in -N(G6)(G6) are the same or different from each other.

[0101] • "halogen atom" Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0102] • "substituted or unsubstituted fluoroalkyl group" The "substituted or unsubstituted heteroalkyl group" described in the present specification means a group in which at least one hydrogen atom of the "substituted or unsubstituted alkyl group" is replaced with a heteroatom, and includes a group in which all hydrogen atoms of the "substituted or unsubstituted alkyl group" are replaced with heteroatoms. Unless otherwise specified, the number of carbon atoms of the "unsubstituted heteroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted heteroalkyl group" means a group in which one or more hydrogen atoms of the "heteroalkyl group" are replaced with a substituent. Note that the "substituted heteroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain of the "substituted heteroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent of the "substituted heteroalkyl group" are further replaced with a substituent. As specific examples of the "unsubstituted heteroalkyl group", examples of a group in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced with a heteroatom, and the like can be given.

[0103] • "Substituted or unsubstituted haloalkyl group" The "substituted or unsubstituted haloalkyl group" described in the present specification means a group in which at least one hydrogen atom of the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and includes a group in which all hydrogen atoms of the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. Unless otherwise specified in the present specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain of the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent of the "substituted haloalkyl group" are further replaced with a substituent. As specific examples of the "unsubstituted haloalkyl group", examples of a group in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced with a halogen atom, and the like can be given. The haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0104] • "Substituted or unsubstituted alkoxy group" The "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -OG3, where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in the present specification, the number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0105] • "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" described in the present specification are groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in the present specification, the "unsubstituted alkylthio group" has a carbon atom number of 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0106] • "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in the present specification are groups represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in the present specification, the "unsubstituted aryloxy group" has a ring-constituting carbon atom number of 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0107] • "Substituted or unsubstituted arylthio group" Specific examples of the "substituted or unsubstituted arylthio group" described in the present specification are groups represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in the present specification, the "unsubstituted arylthio group" has a ring-constituting carbon atom number of 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0108] • "Substituted or unsubstituted trialkylsilyl group" Specific examples of the "trialkylsilyl group" described in the present specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same or different. Unless otherwise specified in the present specification, each alkyl group of the "trialkylsilyl group" has a carbon atom number of 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0109] • "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in the present specification are groups represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced with the "aryl group" as a substituent, and is one way of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with the "unsubstituted aryl group". Unless otherwise specified in the present specification, the "unsubstituted aralkyl group" has a carbon atom number of 7 to 50, preferably 7 to 30, and more preferably 7 to 18.

[0110] Specific examples of the "substituted or unsubstituted aralkyl group" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl, and the like.

[0111] The "substituted or unsubstituted aryl group" described in the present specification is preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, and the like, unless otherwise specified in the present specification.

[0112] The "substituted or unsubstituted heterocyclic group" described in the present specification is preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophenyl, and the like, unless otherwise specified in the present specification.

[0113] In the present specification, the "carbazolyl group" is specifically any one of the following groups, unless otherwise specified in the present specification.

[0114] [Chemical Formula 9] In the present specification, the "(9-phenyl)carbazolyl group" is specifically any one of the following groups, unless otherwise specified in the present specification.

[0115] [Chemical Formula 10] In the aforementioned general formulae (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding site.

[0116] In the present specification, dibenzofuranyl and dibenzothiophenyl are specifically any one of the following unless otherwise specified in the present specification.

[0117] [Chemical 11] In the aforementioned general formulae (TEMP-34) to (TEMP-41), * indicates a bonding site.

[0118] The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like unless otherwise specified in the present specification.

[0119] • "Substituted or unsubstituted arylene group" The "substituted or unsubstituted arylene group" described in the present specification is a divalent group derived by removing one hydrogen atom on the aromatic ring from the above "substituted or unsubstituted aryl group" unless otherwise specified. As specific examples (specific example group G12) of the "substituted or unsubstituted arylene group", there are mentioned a divalent group derived by removing one hydrogen atom on the aromatic ring from the "substituted or unsubstituted aryl group" described in the specific example group G1, and the like.

[0120] • "Substituted or unsubstituted divalent heterocyclic group" The "substituted or unsubstituted divalent heterocyclic group" described in the present specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above "substituted or unsubstituted heterocyclic group" unless otherwise specified. As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", there are mentioned a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in the specific example group G2, and the like.

[0121] • "Substituted or unsubstituted alkylene group" The "substituted or unsubstituted alkylene group" described in the present specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group" unless otherwise specified. As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group", there are mentioned a divalent group derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in the specific example group G3, and the like.

[0122] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise specified in the present specification.

[0123] [Chemical Formula 12] [Chemical Formula 13] In the aforementioned general formulae (TEMP-42) to (TEMP-52), Q1to Q 10 each independently is a hydrogen atom or a substituent.

[0124] In the aforementioned general formulae (TEMP-42) to (TEMP-52), * indicates a bonding site.

[0125] [Chemical Formula 14] In the aforementioned general formulae (TEMP-53) to (TEMP-62), Q1to Q 10 each independently is a hydrogen atom or a substituent.

[0126] Q9and Q 10 may be bonded to each other via a single bond to form a ring.

[0127] In the aforementioned general formulae (TEMP-53) to (TEMP-62), * indicates a bonding site.

[0128] [Chemical Formula 15] In the aforementioned general formulae (TEMP-63) to (TEMP-68), Q1to Q8each independently is a hydrogen atom or a substituent.

[0129] In the aforementioned general formulae (TEMP-63) to (TEMP-68), * indicates a bonding site.

[0130] The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups of the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in the present specification.

[0131] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] In the aforementioned general formulae (TEMP-69) to (TEMP-82), Q1to Q9each independently is a hydrogen atom or a substituent.

[0132] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] In the aforementioned General Formulae (TEMP-83) to (TEMP-102), each of Q1to Q8is independently a hydrogen atom or a substituent.

[0133] The above is a description of the "substituent described in the present specification".

[0134] • "Case where groups each consisting of 2 or more adjacent groups are bonded to form a ring" In the present specification, the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring", the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring", and the "case where 1 or more groups each consisting of 2 or more adjacent groups are not bonded to each other".

[0135] Hereinafter, the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" in the present specification (hereinafter, these cases are sometimes collectively referred to as the "case where groups are bonded to form a ring") will be described. The case of an anthracene compound represented by the following General Formula (TEMP-103) in which the parent skeleton is an anthracene ring will be described.[Chemical Formula 23] .

[0136] For example, in the "case where 1 or more groups each consisting of 2 or more adjacent groups are bonded to form a ring" in R 921 to R 930 , the group consisting of 2 adjacent groups as 1 group is R 921 to R 922 , the group consisting of 2 adjacent groups as 1 group is R 922 to R 923 , the group consisting of 2 adjacent groups as 1 group is R 923 to R 924 , the group consisting of 2 adjacent groups as 1 group is R 924 to R 930 , the group consisting of 2 adjacent groups as 1 group is R 930 to R 925 , the group consisting of 2 adjacent groups as 1 group is R 925 to R 926 , the group consisting of 2 adjacent groups as 1 group is R 926 to R 927 , the group consisting of 2 adjacent groups as 1 group is R927 with the group of R 928 with the group of R 928 with the group of R 929 with the group of R 929 with the group of R 921 with the group of R

[0137] The "1 or more groups" above means that 2 or more groups consisting of 2 or more adjacent groups can simultaneously form a ring. For example, R 921 and R 922 are bonded to each other to form a ring Q A and simultaneously R 925 and R 926 are bonded to each other to form a ring Q B , the anthracene compound represented by the general formula (TEMP-103) above is represented by the following general formula (TEMP-104), [Chemical Formula 24] .

[0138] The case where "a group consisting of 2 or more adjacent groups" forms a ring includes not only the case where a group consisting of "2" adjacent groups is bonded, as in the foregoing example, but also the case where a group consisting of "3 or more" adjacent groups is bonded. For example, it means that R 921 and R 922 are bonded to each other to form a ring Q A , and R 922 and R 923 are bonded to each other to form a ring Q C , a group consisting of 3 groups (R 921 , R 922 , and R 923 ) adjacent to each other are bonded to each other to form a ring, and are fused to the anthracene parent skeleton, at which time, the anthracene compound represented by the general formula (TEMP-103) above is represented by the following general formula (TEMP-105). In the general formula (TEMP-105) below, the ring Q A and the ring Q C share R 922 , [Chemical Formula 25] .

[0139] The "single ring" or "fused ring" formed can be a saturated ring or an unsaturated ring as a structure of a ring formed alone. Even when "1 group of a group consisting of 2 groups adjacent to each other" forms a "single ring" or "fused ring", the "single ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q A and the ring Q B in the general formula (TEMP-104) above are each a "single ring" or "fused ring". In addition, the ring QA and ring Q C is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A and ring Q C is fused to form a fused ring. The ring Q of the aforementioned general formula (TMEP-104) A and ring Q C is fused to form a fused ring. The ring Q of the aforementioned general formula (TMEP-104) A is a monocyclic ring when it is a benzene ring. The ring Q of the aforementioned general formula (TMEP-104) A is a monocyclic ring when it is a benzene ring. The ring Q of the aforementioned general formula (TMEP-104) A is a monocyclic ring when it is a benzene ring. The ring Q of the aforementioned general formula (TMEP-104) A is a fused ring.

[0140] "Unsaturated ring" includes, in addition to aromatic hydrocarbon ring, aromatic heterocyclic ring, aliphatic hydrocarbon ring having an unsaturated bond, i.e., double bond and / or triple bond in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocyclic ring having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). "Saturated ring" includes aliphatic hydrocarbon ring having no unsaturated bond, or non-aromatic heterocyclic ring having no unsaturated bond.

[0141] As a specific example of the aromatic hydrocarbon ring, a structure in which the group exemplified as a specific example in Specific Example Group G1 is capped with a hydrogen atom can be given.

[0142] As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group exemplified as a specific example in Specific Example Group G2 is capped with a hydrogen atom can be given.

[0143] As a specific example of the aliphatic hydrocarbon ring, a structure in which the group exemplified as a specific example in Specific Example Group G6 is capped with a hydrogen atom can be given.

[0144] "Forming a ring" means forming a ring only from a plurality of atoms of the parent skeleton, or from a plurality of atoms of the parent skeleton and further 1 or more arbitrary atoms. For example, the ring Q formed by the mutual bonding of R 921 and R 922 is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A means a ring formed by the carbon atoms of the anthracene skeleton to which R 921 is bonded, the carbon atoms of the anthracene skeleton to which R 922 is bonded, and 1 or more arbitrary atoms. As a specific example, in the case where the ring Q is formed by R 921 and R 922 , the ring formed by R A and R 921 is a monocyclic ring. In the case where the ring Q is formed by R 922 and R 921 , the ring formed by R 922 is a benzene ring.

[0145] Here, "arbitrary atom" is preferably at least one atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise specified in the present specification. For an arbitrary atom (e.g., the case of a carbon atom or a nitrogen atom), a bond not forming a ring can be capped with a hydrogen atom or the like, or can be substituted with a "substituent described later". When an arbitrary atom other than a carbon atom is included, the ring formed is a heterocycle.

[0146] "2 or more arbitrary atoms" constituting a monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less, unless otherwise specified in the present specification.

[0147] "monocyclic" is preferred to "fused ring" in the present specification, unless otherwise specified.

[0148] "unsaturated ring" is preferred to "saturated ring" in the present specification, unless otherwise specified.

[0149] "monocyclic" is preferably a benzene ring in the present specification, unless otherwise specified.

[0150] "unsaturated ring" is preferably a benzene ring in the present specification, unless otherwise specified.

[0151] "1 or more groups consisting of 2 or more adjacent groups" "form a substituted or unsubstituted monocyclic ring" or "form a substituted or unsubstituted fused ring" is preferably 1 or more groups consisting of 2 or more adjacent groups form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of a parent skeleton and 1 or more of 15 or less atoms selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise specified in the present specification.

[0152] The substituent when the above "monocyclic ring" or "fused ring" has a substituent is, for example, a "substituent described later". The specific example of the substituent when the above "monocyclic ring" or "fused ring" has a substituent is the substituent described in the above "substituent described in the present specification".

[0153] The substituent when the above "saturated ring" or "unsaturated ring" has a substituent is, for example, a "substituent described later". The specific example of the substituent when the above "monocyclic ring" or "fused ring" has a substituent is the substituent described in the above "substituent described in the present specification".

[0154] The above is a description of the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups each consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted fused ring" ("case where bonding to form a ring occurs").

[0155] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the aforementioned substituents in the case of "substituted or unsubstituted" (in the present specification, sometimes referred to as "arbitrary substituents") are, for example, groups selected from the following: unsubstituted alkyl having 1 to 50 carbon atoms, unsubstituted alkenyl having 2 to 50 carbon atoms, unsubstituted alkynyl having 2 to 50 carbon atoms, unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O- (R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), halogen atom, cyano group, nitro group, unsubstituted aryl having 6 to 50 ring-forming carbon atoms, and unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Here, R 901 to R 907 are each independently: hydrogen atom, substituted or unsubstituted alkyl having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms, substituted or unsubstituted aryl having 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms; R 901 When two or more R 901 are present, two or more R 901 are the same or different, R 902 When two or more R 902 are present, two or more R 902 are the same or different, R 903 When two or more R 903 are present, two or more R 903 are the same or different, R 904 when two or more exist, two or more of R 904 are the same or different from each other, R 905 when two or more exist, two or more of R 905 are the same or different from each other, R 906 when two or more exist, two or more of R 906 are the same or different from each other, R 907 when two or more exist, two or more of R 907 are the same or different from each other.

[0156] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is a group selected from the group consisting of: an alkyl group having a carbon atom number of 1 to 50, an aryl group having a ring-constituting carbon atom number of 6 to 50, and a heterocyclic group having a ring-constituting atom number of 5 to 50.

[0157] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is a group selected from the group consisting of: an alkyl group having a carbon atom number of 1 to 18, an aryl group having a ring-constituting carbon atom number of 6 to 18, and a heterocyclic group having a ring-constituting atom number of 5 to 18.

[0158] Specific examples of each group of the aforementioned arbitrary substituent are the specific examples of the substituent described in the aforementioned "substituent described in the present specification".

[0159] In the present specification, unless otherwise specified, any arbitrary substituent can form, with each other, a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.

[0160] In the present specification, unless otherwise specified, any arbitrary substituent can further have a substituent. The substituent further possessed by any arbitrary substituent is the same as the aforementioned arbitrary substituent.

[0161] In the present specification, the numerical range using "AA to BB" means a range including the lower limit value of the numerical value recited in front of "AA to BB" as the lower limit value and the upper limit value of the numerical value recited at the back of "AA to BB" as the upper limit value.

[0162] [Organic EL Element] An organic EL element of one embodiment of the present application (hereinafter also referred to as "an organic EL element of the present application") is a concept including a first organic EL element, a second organic EL element, and a third organic EL element which will be described later.

[0163] The first organic EL element of the present application can achieve higher element performance by having the configuration described later. Specifically, an organic EL element with low driving voltage and high efficiency in a range from low current density to high current density can be achieved.

[0164] The second organic EL element of the present application can achieve higher element performance by having the configuration described later. Specifically, an organic EL element with low driving voltage and high efficiency even at low current density can be achieved.

[0165] In one embodiment, the organic EL element of one embodiment of the present application is the first organic EL element.

[0166] In one embodiment, the organic EL element of one embodiment of the present application is the second organic EL element.

[0167] In one embodiment, the organic EL element of one embodiment of the present application is the third organic EL element.

[0168] [First Organic EL Element] The first organic EL element of one embodiment of the present application (hereinafter also referred to as "the first organic EL element of the present application") includes a cathode, an anode, and one or more organic layers provided between the cathode and the anode; at least one of the one or more organic layers includes a first component and a second component.

[0169] The first component is a compound represented by the following formula (1).

[0170] The second component is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex including an alkali metal, an organic metal complex including an alkaline earth metal, and an organic metal complex including a rare earth metal.

[0171] The first organic EL element of the present application can achieve higher element performance by having the configuration described above. Specifically, an organic EL element with low driving voltage and high efficiency in a range from low current density to high current density can be achieved.

[0172] Note that the first component is different from the second component, as is clear from the definitions of the components.

[0173] Next, each configuration of the first organic EL element of one embodiment of the present application is described.

[0174] (First Component) The first component in the first organic EL element of one embodiment of the present application is a compound represented by the following formula (1).

[0175] [Formula 26] In formula (1), R1to R 10 at least one of which is a group represented by formula (1A); R1to R 10 which is not the group represented by the aforementioned formula (1A), is a hydrogen atom or a substituent A; 10 at least three of which are each independently a group represented by the aforementioned formula (1A), a substituent A, or a hydrogen atom which is a deuterium atom; In formula (1A), L 1A is: a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted 2-valent heterocyclic group having 5 to 50 ring-forming atoms; n1A is an integer of 0 to 3; when n1A is 0, (L 1A ) n1A is a single bond; when n1A is 2 or 3, a plurality of L 1A are connected in series to each other, and the structure within the parentheses is bonded to the L 1A which is farthest from the anthracene skeleton; and a plurality of L 1A may be the same or different; X 11A is C(R 21A )(R 22A ), N(R 23A ), O, or S; one group or more groups each consisting of 2 or more adjacent ones of R 11A to R 18A are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or do not form the aforementioned ring; when the aforementioned substituted or unsubstituted monocyclic ring is formed, one of the atoms constituting the monocyclic ring is bonded to L 1A , or one of R 11A to R 18A and one of R 21A to R 23A represent a bond to L 1A ; one of the atoms constituting the fused ring is bonded to L 1A R 11A ~R 18A and R 21A ~R 23A represents a bond to L 1A ; one of R 11A ~R 18A and R 21A ~R 23A represents a bond to L 1A ; R 1A ~R 11A and R 18A ~R 21A do not represent a bond to L 23A and do not form the aforementioned rings; when two or more groups represented by formula (1A) are present, the two or more groups represented by formula (1A) can be the same or different; the substituent A is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 ~R 907 are each independently: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; When two or more substituents A are present, the two or more substituents A can be the same or different from each other; R 901 ~R 907 When two or more R 901 ~R 907 are present, the two or more R wherein the compound represented by the aforementioned formula (1) does not contain, in the molecule, a structure represented by the following formula (M1), a structure represented by the following formula (M2), a structure represented by the following formula (M3), and a structure represented by the following formula (M4); [Chemical Formula 27] .

[0176] In most cases, a compound that has been used as an electron transport material and the like for an organic EL element, which contains a structure represented by formula (M1) to formula (M4) (electron-accepting structure) in the molecule, decreases the external quantum efficiency (EQE) of the organic EL element at a low current density.

[0177] The present inventors have found that, if a compound (a first component in a first organic EL element of one embodiment of the present application) that is different from the aforementioned conventional material, does not contain a structure represented by formula (M1) to formula (M4) in the molecule, and has a total of at least three specified groups or deuterium atoms on an anthracene skeleton is used in combination with a second component described later, it can be used as an electron transport material, and furthermore, an organic EL element using the material has a low driving voltage and does not decrease in EQE in a range from a low current density to a high current density.

[0178] Although the specific mechanism by which the EQE is not decreased in the low current density region is not completely clear, it is believed that, when a compound containing the aforementioned electron-accepting structure in the molecule is used, the influence of voltage is large in the high current density region and the influence of the structure on the EQE is small, but the influence of the structure is large in the low current density region, and the electrons become excessive and destroy the carrier balance, leading to a decrease in the EQE. In contrast, it is believed that, when the first component in the first organic EL element of one embodiment of the present application, which does not contain the aforementioned electron-accepting structure in the molecule, is used, the carrier balance is maintained in a range from a low current density to a high current density, so that the EQE is not decreased.

[0179] In formula (1), at least one of R1to R 10 is a group represented by formula (1A). For example, when R 10 is a group represented by formula (1A), the compound represented by formula (1) is represented by the following formula (Ex1), [Chem. 28] .

[0180] In formula (1), R1to R 10 each independently are a group represented by the aforementioned formula (1A), a substituent A, or a hydrogen atom as a deuterium atom. In other words, R1to R 10 of which are hydrogen atoms as protium atoms are 7 or less.

[0181] Next, the case where "when n1A is 2 or 3, a plurality of L 1A are connected in series with each other, and the structure within the parentheses is bonded to the L 1A which is farthest from the anthracene skeleton" is described. For example, when R 10 is a group represented by formula (1A), and n1A is 3, the compound represented by formula (1) is represented by the following formula (Ex2), .

[0182] In formula (1A), 1 group or more consisting of 2 or more adjacent ones of R 11A to R 18A are bonded to each other to form a substituted or unsubstituted monocyclic ring, 1 of the atoms constituting the monocyclic ring is bonded to L 1A , or R 11A to R 18A and R 21A to R 23A each represent a bond to L 1A .

[0183] The case where "1 of the atoms constituting the monocyclic ring is bonded to L 1A " is described. For example, when a group represented by formula (1A) is a group represented by the following formula (Ex3) in which a group of R 11A and R 12A are bonded to each other to form an unsubstituted benzene ring, 1 of the 4 carbon atoms (carbon atoms with *) constituting the benzene ring is bonded to L 1A , [Chem. 30] .

[0184] Next, the case where "1 of R 11A to R 18A and R 21A to R 23A each represent a bond to L 1A " is described. When a group represented by formula (1A) is a group represented by the aforementioned formula (Ex3) in which a group of R 11A and R 12A are bonded to each other to form an unsubstituted benzene ring,13A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A key.

[0185] X 11A C (R 21A )(R 22A ), R 13A ~R 18A and R 21A ~R 22A 1 in the expression is consistent with L 1A key.

[0186] X 11A N (R 23A ), R 13A ~R 18A and R 23A 1 in the expression is consistent with L 1A key.

[0187] X 11A When it is O or S, R 13A ~R 18A 1 in the expression is consistent with L 1A key.

[0188] In formula (1A), R 11A ~R 18A When two or more adjacent atoms in the condensed ring are bonded to each other to form a substituted or unsubstituted condensed ring, one of the atoms constituting the condensed ring is bonded to L. 1A R that is bonded to or does not contribute to the formation of the fused ring 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A key.

[0189] "One of the atoms constituting the fused ring and L 1A For example, R 11A With R 12A When the groups of L are bonded to each other to form an unsubstituted naphthalene ring, the group represented by formula (1A) is represented by the following formulas (Ex4) to (Ex6). In formulas (Ex4) to (Ex6), one of the six carbon atoms (carbon atoms marked with *) constituting the naphthalene ring is bonded to L 1A bonding, [Chemistry 31] .

[0190] Next, for “R that does not contribute to the formation of the fused ring 11A ~R 18Aand R 21A ~R 23A one of R 1A to L 11A bonded to R 12A to form an unsubstituted naphthalene ring, in the above formulae (Ex4) to (Ex6), one of R 13A to R 18A and R 21A to R 23A represents a bond to L 1A .

[0191] X 11A is C(R 21A )(R 22A ), one of R 13A to R 18A and R 21A to R 22A represents a bond to L 1A .

[0192] X 11A is N(R 23A ), one of R 13A to R 18A and R 23A represents a bond to L 1A .

[0193] X 11A is O or S, one of R 13A to R 18A represents a bond to L 1A .

[0194] "does not contain a structure represented by the following formulae (M1) to (M4) in the molecule" is explained, [Chemical Formula 32] .

[0195] In formulae (M1) to (M4), the wavy line at the end of the bond means that there is an atom before the wavy line. For example, the end of the bond can be a hydrogen atom or a bond to an atom (for example, a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom, etc.) that can have a valence of 2 or more.

[0196] "does not contain a structure represented by formula (M1) to (M4) in the molecule" means that the structure represented by formula (M1) is not contained, the structure represented by formula (M2) is not contained, the structure represented by formula (M3) is not contained, and the structure represented by formula (M4) is not contained at any site in the molecule, for example, does not have the structure as a substituent and does not contain the structure in the parent skeleton.

[0197] Further, the compound containing any one of the structures represented by Formula (M1), the structure represented by Formula (M2), the structure represented by Formula (M3), and the structure represented by Formula (M4) does not correspond to the first component in the first organic EL element of one embodiment of the present application.

[0198] As the substituent group containing the structure represented by Formula (M1), for example, a substituent group represented by the following Formula (M1-1) (unsubstituted imidazolyl group) can be given, [Chemical Formula 33] In Formula (M1-1), * indicates the bonding position of the substituent group.

[0199] In Formula (M1-1), the carbon atom in Formula (M1) corresponds to the carbon atom at position 2 of the imidazole skeleton of Formula (M1-1), and the nitrogen atom in Formula (M1) corresponds to the nitrogen atom at position 3 of the imidazole skeleton of Formula (M1-1). That is, the two wavy lines at the end of the two bonds extending from the carbon atom in Formula (M1) indicate the hydrogen atom bonded to the carbon atom in Formula (M1-1) and the nitrogen atom at position 1 of the imidazole skeleton of Formula (M1-1), and the wavy line at the end of the bond extending from the nitrogen atom in Formula (M1) indicates the carbon atom at position 4 of the imidazole skeleton of Formula (M1-1).

[0200] Thus, the first component in the first organic EL element of one embodiment of the present application does not have an imidazole group and a group having an imidazole skeleton.

[0201] Further, as the compound containing the structure represented by Formula (M1) in a parent skeleton, for example, a compound represented by the following Formula (M1-2) can be given, [Chemical Formula 34] .

[0202] In Formula (M1-2), the carbon atom in Formula (M1) corresponds to the carbon atom at position 2 of the 1H-naphtho[1,2-d]imidazole skeleton of Formula (M1-2), and the nitrogen atom in Formula (M1) corresponds to the nitrogen atom at position 3 of the 1H-naphtho[1,2-d]imidazole skeleton of Formula (M1-2). That is, the two wavy lines at the end of the two bonds extending from the carbon atom in Formula (M1) indicate the hydrogen atom bonded to the carbon atom in Formula (M1-2) (omitted in Formula (M1-2) described above) and the nitrogen atom at position 1 of the 1H-naphtho[1,2-d]imidazole skeleton of Formula (M1-2), and the wavy line at the end of the bond extending from the nitrogen atom in Formula (M1) indicates the carbon atom at position 4 of the 1H-naphtho[1,2-d]imidazole skeleton of Formula (M1-2).

[0203] Thus, the first component in the first organic EL element of one embodiment of the present application does not have an imidazole skeleton. Thus, the first component in the first organic EL element of one embodiment of the present application does not have an imidazole skeleton.

[0204] Here, from formula (M1), it is understood that the front end of the bond extending from the nitrogen atom and the front end of the bond extending from the carbon atom each exist with another atom, and the bond extending from the nitrogen atom and the bond extending from the carbon atom do not become single (identical). In other words, the atom existing at the front end of the wave line at the end of the bond extending from the nitrogen atom does not become the carbon atom bonded to the nitrogen atom through a double bond, and the atom existing at the front end of the wave line at the end of the bond extending from the carbon atom does not become the nitrogen atom bonded to the carbon atom through a double bond. That is, the cyano group in which the nitrogen atom and the carbon atom are bonded through a triple bond does not correspond to the structure represented by formula (M1). Note that, from the definition, it is understood that the cyano group corresponds to the structure represented by formula (M3).

[0205] The structure represented by formula (M2) is derived from a phosphine oxide group, and thus the first component in the first organic EL element of one embodiment of the present application does not include a phosphine oxide group.

[0206] Here, from formula (M2), it is understood that the two or more wave lines at the end of the bond extending from the phosphorus atom do not mean that the same one atom exists at the front end of the two or more wave lines. For example, a case where one carbon atom is not bonded to the phosphorus atom through a double bond is not included. That is, a group represented by the following (M2-1) (a monovalent group derived from a methylene phosphoryl group) does not correspond to the structure represented by formula (M2), and thus the first component in the first organic EL element of one embodiment of the present application can have the structure represented by formula (M2-1), [Chemical Formula 35] In formula (M2-1), * indicates a bonding position of the substituent.

[0207] The structure represented by formula (M3) is derived from a cyano group, and thus the first component in the first organic EL element of one embodiment of the present application does not include a cyano group.

[0208] Here, from formula (M3), it is understood that the wave line at the end of the bond extending from the carbon atom means that one atom exists at the front end of the wave line.

[0209] The structure represented by formula (M4) is derived from a carbonyl group, and thus the first component in the first organic EL element of one embodiment of the present application does not include a carbonyl group.

[0210] Here, from formula (M4), it is understood that the two wave lines at the end of the bond extending from one carbon atom do not mean that the same one atom exists at the front end of the two wave lines. For example, a case where one carbon atom is not bonded to one carbon atom through a double bond is not included. That is, a group represented by the following (M4-1) (a monovalent group derived from an ethenone) does not correspond to the structure represented by formula (M4), and thus the first component in the first organic EL element of one embodiment of the present application can have the structure represented by formula (M4-1), [Chemical Formula 36] In the formula (M4-1), * indicates the bonding position of the substituent.

[0211] Note that, as the substituent A and R 901 ~R 907 does not include the structure represented by the formula (M1) to the formula (M4).

[0212] In the formula (1), as the "divalent heterocyclic group having 5 to 50 ring-forming atoms, which is substituted or unsubstituted," L 1A does not include the structure represented by the formula (M1) to the formula (M4).

[0213] In the formula (1A), "one or more groups each consisting of 2 or more adjacent R 11A ~R 18A bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring" does not include the structure represented by the formula (M1) to the formula (M4).

[0214] In the formula (1) and the formula (1A), the substituent in the case of "substituted or unsubstituted" does not include the structure represented by the formula (M1) to the formula (M4).

[0215] In one embodiment, at least 3 of R1to R 10 are each independently the group represented by the aforementioned formula (1A) or the substituent A.

[0216] In one embodiment, 2 of R1to R 10 are each independently the substituent A, and the other of R1to R 10 is the group represented by the aforementioned formula (1A).

[0217] In one embodiment, R9and R 10 are each independently the group represented by the aforementioned formula (1A) or the substituent A.

[0218] In one embodiment, one of R9and R 10 is the group represented by the aforementioned formula (1A), and the other of R9and R 10 is the substituent A.

[0219] In one embodiment, R2, R9, and R 10 are each independently the group represented by the aforementioned formula (1A) or the substituent A.

[0220] In one embodiment, R9and R 10one of the groups represented by the aforementioned formula (1A), R9and R 10 each of R2and R3independently represents a substituent A.

[0221] In one embodiment, the group represented by the aforementioned formula (1A) is a group represented by any one of the following formulae (1A-1) to (1A-3), [Chem. 37] In formulae (1A-1) to (1A-3), L 1A and n1Aare as defined in formula (1) ; X 11A is C (R 21A ) (R 22A ), N (R 23A ), O or S; R 21A to R 23A , R 111A to R 120A , R 121A to R 130A , and R 131A to R 140A each independently represent a hydrogen atom or a substituent A; R 1A to R 1A , R 21A to R 23A , R 111A to R 120A , R 121A to R 130A , and R 131A to R 140A each independently represent a hydrogen atom or a substituent A; Substituent A is as defined in formula (1).

[0222] In one embodiment, X 11A is O or S.

[0223] In one embodiment, the compound represented by the aforementioned formula (1) is a compound represented by any one of the following formulae (1-1) to (1-3), [Chem. 38] In formulae (1-1) to (1-3), L 1A and n1Aare as defined in formula (1) ; X 111A is O or S; R 12 and R 19 each independently represent a substituent A; R 11 , R13 ~R 18 , R 121A ~R 140A each independently is a hydrogen atom or a substituent A; the substituent A is as defined in formula (1); wherein the compound represented by any one of the aforementioned formulae (1-1) to (1-3) does not contain, within the molecule, a structure represented by the following formula (M1), a structure represented by the following formula (M2), a structure represented by the following formula (M3), and a structure represented by the following formula (M4); [Chemical Formula 39] .

[0224] In one embodiment, L 1A is a single bond.

[0225] In one embodiment, the compound represented by the aforementioned formula (1) is a compound represented by any one of the following formulae (1-11) to (1-41), [Chemical Formula 40] In the formulae (1-11) to (1-41), X 111A is O or S; R 12 , R 13 and R 19 each independently is a substituent A; R 121A ~R 140A each independently is a hydrogen atom or a substituent A; the substituent A is as defined in formula (1); wherein the compound represented by any one of the aforementioned formulae (1-11) to (1-41) does not contain, within the molecule, a structure represented by the following formula (M1), a structure represented by the following formula (M2), a structure represented by the following formula (M3), and a structure represented by the following formula (M4); [Chemical Formula 41] .

[0226] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is selected from: an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring-forming carbon atoms, an alkoxy group having 1 to 50 carbon atoms, alkyl group having 1 to 50 carbon atoms, aryloxy group having 6 to 50 ring-forming carbon atoms, arylthio group having 6 to 50 ring-forming carbon atoms, aralkyl group having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -S(=O)2R 46 , -Ge(R 49 )(R 50 )(R 51 ), -N(R 52 )(R 53 ), hydroxy group, halogen atom, nitro group, aryl group having 6 to 50 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0227] R 41 to R 43 , R 46 , and R 49 to R 53 are each independently a hydrogen atom, an alkoxy group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms. 41 R 43 , R 46 , and R 49 to R 53 may be the same or different from each other. 41 R 43 , R 46 , and R 49 to R 53 may be the same or different from each other.

[0228] In one embodiment, the substituents in the case of "substituted or unsubstituted" in Formula (1) are selected from: alkyl group having 1 to 50 carbon atoms, aryl group having 6 to 50 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0229] In one embodiment, the substituents in the case of "substituted or unsubstituted" in Formula (1) are selected from: alkyl group having 1 to 18 carbon atoms, aryl group having 6 to 18 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 18 ring-forming atoms.

[0230] In the present specification, a hydrogen atom being a deuterium atom means that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the naturally occurring ratio. The ratio of deuterium atoms to the total of protium atoms and deuterium atoms can be confirmed by a nuclear magnetic resonance device.

[0231] The compound represented by Formula (1) can be synthesized by using an existing reaction, a raw material, and the like corresponding to the target.

[0232] Hereinafter, although specific examples of the compound represented by Formula (1) are described, they are merely examples, and the compound of one embodiment of the present application is not limited to the following specific examples.

[0233] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53] .

[0234] (Second Component) The second component in the first organic EL element of one embodiment of the present application is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex including an alkali metal, an organic metal complex including an alkaline earth metal, and an organic metal complex including a rare earth metal.

[0235] As the alkali metal, lithium, sodium, potassium, rubidium, cesium, and francium can be given.

[0236] As the alkaline earth metal, beryllium, magnesium, calcium, strontium, barium, and radium can be given. In one embodiment, the alkaline earth metal is one or more metals selected from the group consisting of calcium, strontium, barium, and radium.

[0237] As the rare earth metal, scandium, yttrium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium can be given.

[0238] As the alkali metal compound, alkali metal oxides such as Li2O, Cs2O, K2O, alkali metal halides such as LiF, NaF, CsF, KF, and the like can be given.

[0239] As the alkaline earth metal compound, BaO, SrO, CaO, and Ba x Sr 1-x O (0 < x < 1), Ba x Ca 1-x O (0 < x < 1), and the like can be given.

[0240] As the rare earth metal compound, YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, TbF3, and the like can be given.

[0241] As the organic metal complex containing the alkali metal, the organic metal complex containing the alkaline earth metal, and the organic metal complex containing the rare earth metal, there is no particular limitation as long as at least one of the alkali metal ion, the alkaline earth metal ion, and the rare earth metal ion is contained as the metal ion, respectively. Further, the ligand can be given by hydroxyquinoline, benzo-hydroxyquinoline, hydroxyacridinol, hydroxyphenanthridinol, hydroxyphenyl-oxazole, hydroxyphenyl-thiazole, hydroxydiaryl-oxadiazole, hydroxydiaryl-thiadiazole, hydroxyphenyl-pyridine, hydroxyphenyl-benzimidazole, hydroxybenzotriazole, hydroxyfluoroborane, bipyridine, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketone, azomethine, and derivatives thereof, and the like.

[0242] As the organic metal complex containing the alkali metal, lithium 8-hydroxyquinolate (Liq), for example, can be given.

[0243] In one embodiment, the aforementioned second component is selected from the group consisting of the alkali metal, the alkali metal compound, and the organic metal complex containing the alkali metal.

[0244] In one embodiment, the aforementioned second component is lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 8-hydroxyquinolate (Liq), or lithium oxide (LiO x).

[0245] The proportion of the first component and the second component in the layer (hereinafter, also referred to as "layer A") containing the first component and the second component is not particularly limited, and in one embodiment, the proportion of the first component can be 30 to 70 mass% or 40 to 60 mass% with respect to the total of the aforementioned first component and the aforementioned second component.

[0246] The layer A can contain or not contain components other than the first component and the second component.

[0247] In one embodiment, the layer A contains substantially only the first component and the second component.

[0248] "Substantially only the first component and the second component" means that the layer A does not contain other components at all or contains a trace amount of other components within a range that does not impair the effects of the present application. For example, a case where other components are mixed in the form of unavoidable impurities is included in the embodiment.

[0249] In one embodiment, 80 mass% or more, 90 mass% or more, 95 mass% or more, 99 mass% or more, 99.5 mass% or more, 99.9 mass% or more, 99.99 mass% or more, or 100 mass% of the layer A is the first component and the second component.

[0250] In one embodiment, 80 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, 99.5 mol% or more, 99.9 mol% or more, 99.99 mol% or more, or 100 mol% of the layer A is the first component and the second component.

[0251] In one embodiment, the layer A contains only the first component and the second component.

[0252] [Second Organic EL Element] The second organic EL element of one embodiment of the present application includes a cathode, an anode, and one or more organic layers provided between the cathode and the anode; at least one of the one or more organic layers contains a first component and a second component.

[0253] The first component is a compound satisfying the following formula (R1) and formula (R2), and is a compound that does not contain a structure represented by formula (M1) to formula (M4) in a molecule.

[0254] The second component is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex containing an alkali metal, an organic metal complex containing an alkaline earth metal, and an organic metal complex containing a rare earth metal.

[0255] The second organic EL element according to one embodiment of the present invention can achieve higher element performance by having the above-described configuration. Specifically, it can realize an organic EL element that has a low driving voltage and high efficiency even at low current density.

[0256] It should be noted that, as is clear from the definitions of the components, the first component and the second component are different.

[0257] Hereinafter, each structure of the second organic EL element according to one embodiment of the present invention will be described.

[0258] <First ingredient> The first component in the second organic EL device of one embodiment of the present invention is a compound satisfying the following formulas (R1) and (R2) and does not contain structures represented by the following formulas (M1) to (M4) in the molecule.

[0259] 40mV / nm≤GSP_slope・・・(R1) -2.80eV<LUMO<-1.86eV・・・(R2) [Chemistry 54] In formula (R1), GSP_slope represents the giant surface potential gradient; in formula (R2), LUMO represents the energy level of the lowest unoccupied orbital.

[0260] (Equation (R1): GSP_slope) GSP stands for Giant Surface Polarization. As described later, GSP is generally proportional to film thickness. To operate as a value independent of film thickness, GSP_slope (GSP gradient), the value obtained by dividing GSP by film thickness, is used in formula (R1). GSP_slope is measured using the method described in the Examples.

[0261] GSP is the potential generated on the surface of an organic layer (layer) such as an organic EL element due to the slight alignment of the dipole moments of organic molecules. It is generally known to be proportional to the film thickness. When a potential exists on the surface of a film, an opposite charge is injected to cancel it out. Therefore, GSP can be considered a physical property that directly affects the amount of charge injected.

[0262] The amount of charge injection is one of the key indicators for optimizing the carrier balance between electrons and holes within each layer of an organic EL device, thereby enhancing device performance. Conventionally, the ease of charge injection has been estimated based on the energy difference between the LUMO (Lowest Unoccupied Molecular Electron Molecular Molecular) of each layer and the adjacent layer. However, there are cases where the LUMO alone cannot provide sufficient information.

[0263] On the other hand, GSP directly affects the amount of charge injection, and thus it is considered that there is a correlation between GSP and carrier balance. Therefore, the present inventors and others introduced the aforementioned GSP_slope as a new property value related to carrier balance and conducted a study, and as a result, it was found that if a compound exhibiting a GSP_slope of a certain value or more is used in an organic EL element, negative polarization occurs on the anode side, and the amount of hole injection is improved. In addition, it was also found that the carrier balance in the low current density region is improved, and the decrease in EQE is suppressed.

[0264] The compounds used as electron transport materials and the like for organic EL elements in the related art, which include the structures (electron accepting structures) represented by Formula (M1) to Formula (M4) in the molecules, decrease the EQE at low current densities in many cases. As a reason therefor, according to the research by the present inventors and others, it is considered that the amount of electron injection in the low current density region of the compound is excessive, and the holes combined with the injected electrons become insufficient, and thus the carrier balance factor becomes small, and the EQE decreases. Note that the relationship between the carrier balance and the external quantum efficiency (EQE) of an organic EL element is shown in the following formula.

[0265] EQE = γ χ Φ η In the formula, γ represents the carrier balance factor, χ represents the exciton generation probability (TTF efficiency), Φ represents the light emission quantum yield of the dopant material, and η represents the light extraction efficiency.

[0266] On the other hand, when a compound (a compound satisfying Formula (R1)) exhibiting a certain value or more of GSP_slope, which is different from the above-described conventional material, is used, the amount of hole injection can be ensured to be sufficient from the low current density due to the excellent hole injection ability thereof, and the above-described problem of the decrease in EQE can be solved.

[0267] The upper limit of GSP_slope is not particularly limited, and when GSP_slope is excessively large, the amount of carrier injection is excessively increased, and as a result, the decrease in EQE can occur.

[0268] In one embodiment, the aforementioned first component satisfies the following Formula (R1-1).

[0269] GSP_slope ≤ 60 mV / nm (R1-1) In Formula (R1-1), GSP_slope is as defined in the aforementioned Formula (R1).

[0270] In one embodiment, the aforementioned first component satisfies the following Formula (R1-2).

[0271] 41 mV / nm ≤ GSP_slope (R1-2) In formula (R1-2), GSP_slope is as defined in the aforementioned formula (R1).

[0272] In one embodiment, the aforementioned first component satisfies the following formula (R1-3).

[0273] 41 mV / nm ≤ GSP_slope ≤ 60 mV / nm... (R1-3) In formula (R1-3), GSP_slope is as defined in the aforementioned formula (R1).

[0274] In one embodiment, the aforementioned first component satisfies the following formula (R1-4).

[0275] 42 mV / nm ≤ GSP_slope ≤ 51 mV / nm... (R1-4) In formula (R1-4), GSP_slope is as defined in the aforementioned formula (R1).

[0276] In one embodiment, the GSP_slope of the first component is 41 mV / nm or more, or 42 mV / nm or more.

[0277] In one embodiment, the GSP_slope of the first component is 58 mV / nm or less, 56 mV / nm or less, 54 mV / nm or less, or 52 mV / nm or less.

[0278] (Formula (R2): LUMO) LUMO means the energy level of the lowest unoccupied molecular orbital. The LUMO is measured by the method described in the examples.

[0279] By using a compound satisfying formula (R2) in at least one layer of the organic layer of an organic EL element, the energy barrier at the time of electron injection into a layer adjacent to the layer can be reduced. By this means, an organic EL element having a low driving voltage can be realized.

[0280] In one embodiment, the aforementioned first component satisfies the following formula (R2-1).

[0281] -2.60 eV ≤ LUMO ≤ -2.00 eV... (R2-1) In formula (R2-1), LUMO is as defined in the aforementioned formula (R2).

[0282] In one embodiment, the aforementioned first component satisfies the following formula (R2-2).

[0283] -2.26 eV ≤ LUMO ≤ -2.09 eV... (R2-2) In Formula (R2-2), LUMO is as defined in the aforementioned Formula (R2).

[0284] In one embodiment, the LUMO of the first component is -1.90 eV or less, -1.95 eV or less, -2.00 eV or less, -2.05 eV or less, or -2.09 eV or less.

[0285] In one embodiment, the LUMO of the first component is -2.80 eV or more, -2.70 eV or more, -2.60 eV or more, -2.50 eV or more, -2.40 eV or more, -2.30 eV or more, or -2.26 eV or more.

[0286] In one embodiment, the aforementioned first component satisfies the aforementioned Formula (R1-3) and the aforementioned Formula (R2-2).

[0287] For "not containing a structure represented by the aforementioned Formula (M1) to Formula (M4) in the molecule", matters described in the first organic EL element of one embodiment of the present application can be applied.

[0288] The first component in the second organic EL element of one embodiment of the present application can be synthesized by using a known reaction, a raw material corresponding to the target.

[0289] Hereinafter, specific examples of the first component in the second organic EL element of one embodiment of the present application will be described, which are merely examples, and the first component is not limited to the following specific examples. [Formula 55] .

[0290] Second Component The second component in the second organic EL element of one embodiment of the present application is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex containing an alkali metal, an organic metal complex containing an alkaline earth metal, and an organic metal complex containing a rare earth metal.

[0291] For the second component in the second organic EL element of one embodiment of the present application, matters described in the second component in the first organic EL element of one embodiment of the present application can be applied.

[0292] The proportion of the first component to the second component in a layer containing the first component and the second component (hereinafter also referred to as "layer A") is not particularly limited. For the layer A, matters described in the first organic EL element of one embodiment of the present application can be applied.

[0293] Reference Figure 1A schematic configuration of an organic EL element (first organic EL element and second organic EL element) of one embodiment of the present application will be described.

[0294] An organic EL element 1 of one embodiment of the present application includes a substrate 2, an anode 3, a light-emitting layer 5 as an organic layer, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10.

[0295] Each of the organic layer 4 and the organic layer 6 can be a single layer or can be formed of a plurality of layers.

[0296] In one embodiment, an organic EL element of one embodiment of the present application includes, in the stated order, an anode, a light-emitting layer, an electron-transport region, and a cathode; at least one layer in the electron-transport region includes the first component and the second component (a combination of the first component in the first organic EL element of one embodiment of the present application and the second component in the first organic EL element of one embodiment of the present application, or a combination of the first component in the second organic EL element of one embodiment of the present application and the second component in the second organic EL element of one embodiment of the present application).

[0297] (Electron-transport region) The electron-transport region refers to a total of one layer or two or more layers provided between the light-emitting layer and the cathode. The electron-transport region is, for example, composed of layers each of which is referred to as a hole-blocking layer, an electron-transport layer, and an electron-injection layer, which will be described later, from the light-emitting layer side, and can be a layered structure including all of them or can be a layer structure including only a part of them. Alternatively, two or more layers can be used for each of the layers, for example, two electron-transport layers having different compositions can be stacked.

[0298] Each layer can be formed using only one material or can be formed using two or more materials in combination.

[0299] A layered structure of the electron-transport region in an organic EL element of one embodiment of the present application is exemplified below.

[0300] (a) (light-emitting layer / ) first layer (electron-transport layer) / second layer (electron-injection layer) ( / cathode) (b) (light-emitting layer / ) third layer (hole-blocking layer) / first layer (electron-transport layer) / second layer (electron-injection layer) ( / cathode) (c) (light-emitting layer / ) third layer (hole-blocking layer) / fourth layer (first electron-transport layer) / first layer (second electron-transport layer) / second layer (electron-injection layer) ( / cathode) In one embodiment, the electron-transport region includes, in the stated order from the light-emitting layer side, at least a first layer and a second layer, The aforementioned layer 2 contains the aforementioned component 1 and the aforementioned component 2 (a combination of the component 1 in the first organic EL element of one embodiment of the present application and the component 2 in the first organic EL element of one embodiment of the present application, or a combination of the component 1 in the second organic EL element of one embodiment of the present application and the component 2 in the second organic EL element of one embodiment of the present application).

[0301] In one embodiment, the aforementioned layer 2 substantially contains no compound including the structure represented by the aforementioned formula (M1) in a molecule, compound including the structure represented by the aforementioned formula (M2) in a molecule, compound including the structure represented by the aforementioned formula (M3) in a molecule, and compound including the structure represented by the aforementioned formula (M4) in a molecule.

[0302] "Substantially contains no" means that the layer 2 contains no other component at all or contains a small amount of other component within a range not to impair the effects of the present application. For example, the case where other component is mixed as an inevitable impurity is included in the present embodiment.

[0303] In one embodiment, the aforementioned layer 2 substantially contains only the aforementioned component 1 and the aforementioned component 2 (substantially contains only a combination of the component 1 in the first organic EL element of one embodiment of the present application and the component 2 in the first organic EL element of one embodiment of the present application, or substantially contains only a combination of the component 1 in the second organic EL element of one embodiment of the present application and the component 2 in the second organic EL element of one embodiment of the present application).

[0304] "Substantially contains only the component 1 and the component 2" means that the layer 2 contains no other component at all or contains a small amount of other component within a range not to impair the effects of the present application. For example, the case where other component is mixed as an inevitable impurity is included in the present embodiment.

[0305] (Other components of the organic EL element) The organic EL element of one embodiment of the present application can use a material and an element structure conventionally known without impairing the effects of the present application, as long as the one or two or more organic layers provided between the aforementioned cathode and the aforementioned anode satisfy the above conditions.

[0306] Next, an element structure of the organic EL element of one embodiment of the present application, a material forming each layer, and the like are described.

[0307] As a representative element structure of the organic EL element, a structure in which the following structures are stacked over a substrate can be given.

[0308] (1) Anode / light-emitting layer / electron-transport region / cathode (2) Anode / hole-transport region / light-emitting layer / electron-transport region / cathode (" / ' indicates that the layers are adjacent and stacked.) (hole transport region) The hole transport region is a collective term for one layer or two or more layers disposed between the anode and the light-emitting layer. The hole transport region is composed of, for example, layers referred to as an electron-blocking layer, a hole-transporting layer, and a hole-injecting layer, which will be described later, from the light-emitting layer side, and can be a stacked structure including all of them, or can be composed of only a part of them. In addition, two or more layers can be used for each of the above layers, and, for example, two hole-transporting layers composed of different materials can be stacked.

[0309] Each layer can be formed using only one material, or can be formed using two or more materials in combination.

[0310] Hereinafter, each layer of the organic EL element of one embodiment of the present application will be described.

[0311] (substrate) The substrate serves as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, or the like can be used. In addition, a flexible substrate can be used. The flexible substrate refers to a substrate that is bendable (flexible), and a plastic substrate formed of polycarbonate, polyvinyl chloride, or the like can be given as an example.

[0312] (anode) The anode formed on the substrate is preferably formed using a metal, an alloy, a conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, or the like can be given. In addition, gold (Au), platinum (Pt), or a nitride of a metal material (e.g., titanium nitride), or the like can be given.

[0313] (hole-injecting layer) The hole-injecting layer is a layer containing a substance having a high hole-injecting property. As the substance having a high hole-injecting property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, an aromatic amine compound, or a high molecular compound (oligomer, dendrimer, polymer, or the like), or the like can be used.

[0314] (hole-transporting layer) The hole-transport layer is a layer containing a substance having a high hole-transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used in the hole-transport layer. A high molecular compound such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), or the like can also be used. Among them, a substance having a higher hole-transport property than an electron-transport property can be used in addition to the above substances. Note that the layer containing a substance having a high hole-transport property is not necessarily a single layer, and can be a layer in which layers containing the above substances are stacked.

[0315] (Object (dopant) material of light-emitting layer) The light-emitting layer is a layer containing a substance having a high light-emitting property, and various materials can be used. For example, as the substance having a high light-emitting property, a fluorescent compound that emits fluorescent light, a phosphorescent compound that emits phosphorescent light can be used. The fluorescent compound is a compound that can emit light from a singlet excited state, and the phosphorescent compound is a compound that can emit light from a triplet excited state.

[0316] As the blue fluorescent light-emitting material that can be used in the light-emitting layer, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used. As the green fluorescent light-emitting material that can be used in the light-emitting layer, an aromatic amine derivative or the like can be used. As the red fluorescent light-emitting material that can be used in the light-emitting layer, a xanthene derivative, a diamine derivative, or the like can be used.

[0317] As the blue phosphorescent light-emitting material that can be used in the light-emitting layer, a metal complex such as an iridium complex, an osmium complex, a platinum complex, or the like is used. As the green phosphorescent light-emitting material that can be used in the light-emitting layer, an iridium complex or the like is used. As the red phosphorescent light-emitting material that can be used in the light-emitting layer, a metal complex such as an iridium complex, a platinum complex, a terbium complex, an europium complex, or the like is used.

[0318] (Host material of light-emitting layer) As the light-emitting layer, a structure in which the above substance having a high light-emitting property (guest material) is dispersed in another substance (host material) can be employed. As the substance for dispersing the substance having a high light-emitting property, various substances can be used, and a substance having a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the substance having a high light-emitting property is preferably used.

[0319] As a substance (host material) for dispersing a substance having high light emission, a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a perylene derivative, or an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative can be used.

[0320] In addition, as the host material, a compound having delayed fluorescence (thermally activated delayed fluorescence) can also be used. The light-emitting layer preferably contains the material used in the present application described above and a host compound having delayed fluorescence.

[0321] (Electron-blocking layer, hole-blocking layer, exciton-blocking layer) An electron-blocking layer, a hole-blocking layer, an exciton (triplet) -blocking layer, or the like can be provided adjacent to the light-emitting layer.

[0322] The electron-blocking layer is a layer having a function of blocking the emission of electrons from the light-emitting layer to the hole-transporting layer. The hole-blocking layer is a layer having a function of blocking the emission of holes from the light-emitting layer to the electron-transporting layer. The exciton-blocking layer is a layer having a function of blocking the diffusion of excitons generated in the light-emitting layer to the adjacent layer and confining the excitons in the light-emitting layer.

[0323] (Electron-transporting layer) The electron-transporting layer is a layer containing a substance having high electron-transporting property. In the electron-transporting layer, a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, a oxazine derivative, a carbazole derivative, or a phenanthroline derivative, or a high molecular compound can be used.

[0324] (Electron-injecting layer) The electron-injecting layer is a layer containing a substance having high electron-injecting property. In the electron-injecting layer, a metal complex such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline-lithium (Liq), or the like, an alkali metal or an alkaline earth metal such as lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or francium (Fr), or a compound thereof can be used. x ) can be used.

[0325] (Cathode) The cathode preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, each of which has a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include an alkali metal belonging to Group 1 or Group 2 of the periodic table, such as lithium (Li) and cesium (Cs), an alkaline earth metal, such as magnesium (Mg), calcium (Ca), and strontium (Sr), and an alloy containing the same (e.g., MgAg, AlLi), a rare earth metal, such as europium (Eu) and ytterbium (Yb), and an alloy containing the same.

[0326] In one embodiment of the present application, the film thickness of each layer in the organic EL element is not particularly limited, and is typically preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, to suppress the applied voltage to be low, and to have good luminous efficiency.

[0327] [Method for manufacturing organic EL element] In one embodiment of the present application, the method for forming each layer in the organic EL element is not particularly limited. A publicly known method based on a vacuum evaporation method, a spin coating method, or the like can be used. Each layer such as a light-emitting layer can be formed by a publicly known method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or a coating method based on an immersion method, a spin coating method, a flow coating method, a bar coating method, a roll coating method, or the like of a solution dissolved in a solvent.

[0328] [First composition] The first composition of one embodiment of the present application includes a first component and a second component.

[0329] The aforementioned first component is a compound represented by the above formula (1).

[0330] The aforementioned second component is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex containing an alkali metal, an organic metal complex containing an alkaline earth metal, and an organic metal complex containing a rare earth metal.

[0331] The first component and the second component in the first composition of one embodiment of the present application are as described in the above first organic EL element of one embodiment of the present application.

[0332] The form of the composition is not particularly limited, and examples include a solid, a solution, and a film (layer). As the film (layer), examples include an organic layer (e.g., a hole-blocking layer, an electron-transporting layer, an electron-injecting layer) included in an organic EL element.

[0333] [Second composition] The second composition of one embodiment of the present application includes a first component and a second component.

[0334] The aforementioned first component is a compound satisfying the above formula (R1) and formula (R2), and is a compound that does not contain a structure represented by the above formula (M1) to formula (M4) in the molecule.

[0335] The aforementioned second component is selected from an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a rare earth metal, a rare earth metal compound, an organic metal complex containing an alkali metal, an organic metal complex containing an alkaline earth metal, and an organic metal complex containing a rare earth metal.

[0336] The first component and the second component in the second composition of one embodiment of the present application are as described above in the second organic EL element of one embodiment of the present application.

[0337] The form of the composition is not particularly limited, and examples include a solid, a solution, and a film (layer). As the film (layer), examples include an organic layer (e.g., a hole-blocking layer, an electron-transporting layer, an electron-injecting layer) that constitutes an organic EL element.

[0338] [Electronic device] An electronic device of one embodiment of the present application is characterized by including an organic EL element of one embodiment of the present application or a third organic EL element described later.

[0339] Specific examples of the electronic device include a display component such as an organic EL panel assembly; a display device such as a television, a mobile phone, or a personal computer; and a light-emitting device such as a lighting or a vehicle lamp.

[0340] [Novel compound] One embodiment of the present application relates to a compound represented by the following formula (2).

[0341] [Formula 56] In formula (2), Ring a is: a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 6 to 50 ring-forming atoms; R 101 ~R 107 , R 111 ~R 113 , R 121 ~R 125 , and R 131 ~R 135 each independently represents a hydrogen atom or a substituent R; wherein at least one of R 111 ~R 113 is a substituent R, or the aforementioned ring a has at least one substituent; the substituent R is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O- (R 904 ), -S- (R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 to R 907 each independently are: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms; R 901 to R 907 when two or more exist, two or more of R 901 to R 907 may be the same or different; when two or more of the substituents R exist, two or more of the substituents R can be the same or different.

[0342] In formula (2), ring a forms a fused ring with the benzofuran skeleton. That is, ring a has at least one carbon-carbon bond, and shares this carbon-carbon bond with the benzofuran skeleton.

[0343] In one embodiment, ring a includes a six-membered ring structure having at least one carbon-carbon bond, and shares this carbon-carbon bond with the benzofuran skeleton.

[0344] In one embodiment, the compound represented by the aforementioned formula (2) is a compound represented by the following formula (2-1).

[0345] [Compound 57] In formula (2-1), R 101 ~R 107 , R 111 ~R 119 , R 121 ~R 125 , and R 131 ~R 135 are each independently a hydrogen atom or a substituent R; 111 at least one of R 119 ~R The substituent R is as defined in the aforementioned formula (2).

[0346] In one embodiment, the compound represented by the aforementioned formula (2) is a compound represented by the following formula (2-11), [Chem. 58] In formula (2-11), R 101 ~R 107 , R 111 ~R 115 , R 117 ~R 119 , R 121 ~R 125 , R 131 ~R 135 , and R 141 ~R 145 are each independently a hydrogen atom or a substituent R; The substituent R is as defined in the aforementioned formula (2).

[0347] In one embodiment, the substituent R is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0348] In one embodiment, the substituent R is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0349] In one embodiment, R 101 ~R 107 , R 111 ~R 115 , R 117 ~R 119 , R 121 ~R 125 , R 131 ~R 135 , and R 141 ~R 145 are hydrogen atoms.

[0350] In one embodiment, the compound represented by the aforementioned formula (2) contains at least one deuterium atom.

[0351] In one embodiment, one or more hydrogen atoms selected from the group consisting of: R as a hydrogen atom 101 ~R 107 , R as a substituent R 101 ~R 107 having a hydrogen atom, R as a hydrogen atom 111 ~R 113 , R as a substituent R 111 ~R 113 having a hydrogen atom, R as a hydrogen atom 121 ~R 125 , R as a substituent R 125 ~R 125 having a hydrogen atom, R as a hydrogen atom 131 ~R 135 , R as a substituent R 131 ~R 135 having a hydrogen atom, a hydrogen atom possessed by ring a (including a hydrogen atom possessed by a substituent possessed by ring a).

[0352] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (2) is selected from the group consisting of: an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring-forming carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring-forming carbon atoms, an arylthio group having 6 to 50 ring-forming carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 , -COOR 45 , -S(=O)2R 46 , -P(=O)(R 47 )(R 48 ), -Ge(R 49 )(R 50 )(R 51 ), -N(R 52 )(R 53 ), hydroxy group, halogen atom, cyano group, nitro group, aryl group having 6 to 50 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0353] R 41 to R 43 , R 46 , and R 49 to R 53 are each independently a hydrogen atom, an alkoxy group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms. 41 R 43 to R 46 , R 49 , and R 53 to R 41 may be the same or different. 43 46 49 53

[0354] In one embodiment, the substituents in the case of "substituted or unsubstituted" in Formula (2) are selected from: alkyl group having 1 to 50 carbon atoms, aryl group having 6 to 50 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0355] In one embodiment, the substituents in the case of "substituted or unsubstituted" in Formula (2) are selected from: alkyl group having 1 to 18 carbon atoms, aryl group having 6 to 18 ring-forming carbon atoms, and monovalent heterocyclic group having 5 to 18 ring-forming atoms.

[0356] The compound of one embodiment of the present application can be synthesized by using a known reaction, a raw material corresponding to the target. ​​​​

[0357] Specific examples of the compound represented by formula (2) include those of the specific examples of the compound represented by formula (1) described above that satisfy formula (2).

[0358] [3rd Organic EL Element] A 3rd organic EL element of one embodiment of the present application includes a cathode, an anode, and one or more organic layers provided between the cathode and the anode; at least one of the one or more organic layers includes a compound represented by formula (2).

[0359] For other components of the 3rd organic EL element, at least one of the one or more organic layers includes a compound represented by formula (2) in place of a compound represented by formula (1), and the description of the "1st organic EL element of one embodiment of the present application" can be applied except for this. Examples

[0360] <Compound> A first component used in the production of the organic EL element of the examples is described below.

[0361] [Chemical Formula 59] [Chemical Formula 60] A comparative example compound used in the production of the organic EL element of the comparative example is described below, [Chemical Formula 61] [Chemical Formula 62] .

[0362] A second component used in the production of the organic EL element of the examples and the comparative example is described below, [Chemical Formula 63] 8-hydroxyquinoline lithium (Liq).

[0363] Structures of other compounds used in the production of the organic EL element of the examples and the comparative example are described below, [Chemical Formula 64] [Chemical Formula 65] .

[0364] Example 1 <Production of Organic EL Element> An organic EL element was produced as follows.

[0365] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatics Corporation) having an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was made to be 130 nm.

[0366] The cleaned glass substrate having a transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and first, on the side on which the transparent electrode was formed, compound HT-1 and HA were co-deposited in such a manner that the proportion of compound HA reached 3 mass%, in a manner so as to cover the transparent electrode, to form a first hole transport layer having a film thickness of 10 nm.

[0367] Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 80 nm.

[0368] Compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer having a film thickness of 5 nm.

[0369] On the third hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited in such a manner that the proportion of compound BD-1 reached 1 mass%, to form a light-emitting layer having a film thickness of 20 nm.

[0370] Compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer having a film thickness of 5 nm.

[0371] On the first electron transport layer, compound 1-1 and lithium 8-hydroxyquinolinate (Liq) were co-deposited in such a manner that the proportion of Liq reached 50 mass%, to form a second electron transport layer having a film thickness of 25 nm.

[0372] Metal Yb was deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.

[0373] Metal Al was deposited on the electron injection layer to form a cathode having a film thickness of 50 nm.

[0374] The element configuration of the organic EL element of Example 1 is briefly represented as follows.

[0375] ITO (130) / HT-1:HA (10:3%) / HT-1 (80) / HT-2 (5) / BH-1:BD-1 (20:1%) / ET-1 (5) / Compound 1-1:Liq (25:50%) / Yb (1) / Al (50) The numbers in parentheses represent the film thickness (unit: nm). Also, the numbers in parentheses expressed in percentages represent the proportion (mass%) of the latter compound in the layer.

[0376] < Evaluation of Organic EL Element > The produced organic EL elements were subjected to the following evaluations. The results are shown in Table 1.

[0377] Drive voltage At room temperature, a DC constant current of 10 mA / cm 2 The initial characteristics of the organic EL elements were measured.

[0378] EQE The organic EL elements were subjected to voltage application in such a manner that the current density reached 10 mA / cm 2 EL emission spectrum was measured with a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). External quantum efficiency (EQE) (%) was calculated from the obtained spectroradiometer spectrum. Hereinafter, this is referred to as "EQE at 10 mA / cm 2

[0379] Next, the organic EL elements were subjected to voltage application in such a manner that the current density reached 0.1 mA / cm 2 EQE (%) was calculated in the same manner except for this, and hereinafter, this is referred to as "EQE at 0.1 mA / cm 2

[0380] The EQE ratio was calculated based on the following relational expression.

[0381] EQE ratio = (EQE at 0.1 mA / cm 2 ) / (EQE at 10 mA / cm 2 ) Examples 2 to 3 In the formation of the second electron transport layer, the compound shown in Table 1 was used instead of Compound 1-1, and otherwise, the organic EL elements were produced and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0382] Comparative Examples 1 to 5 In the formation of the second electron transport layer, the compound shown in Table 1 was used instead of Compound 1-1, and otherwise, the organic EL elements were produced and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0383] [Table 1] ​​Comparative Example 1 is an organic EL element using a compound (Compound Ref 1-1) that has been used as an electron transporting material or the like for an organic EL element in the past, which includes a structure (electron-accepting structure) represented by Formula (M1) in the molecule. The EQE ratio is low, and the EQE decreases at low current density. This is considered to be due to the fact that, in the low current density region, the influence of the electron-accepting structure is large compared to the high current density region, and the electrons become excessive, thereby destroying the carrier balance.

[0384] Furthermore, the EQE ratios of the organic EL elements of Comparative Examples 2 to 5, which use compounds that do not satisfy the specific structural condition, are also low.

[0385] The first organic EL elements of the present application (Examples 1 to 3), which use compounds that satisfy the specific structural condition, show the same degree of driving voltage as the organic EL elements of Comparative Examples 1 to 5, and also show the same degree of EQE at high current density (10 mA / cm 2 ). On the other hand, at low current density (0.1 mA / cm 2 ), the organic EL elements of Examples 1 and 2 show the same degree of EQE as the EQE at high current density (10 mA / cm 2 ), whereas the organic EL elements of Comparative Examples 1 to 5 show low EQE.

[0386] Example 4 <Production of Organic EL Element> An organic EL element was produced as described below.

[0387] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatics Corporation) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO was made to be 130 nm.

[0388] The glass substrate with the transparent electrode after cleaning was mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, on the side on which the transparent electrode was formed, compound HT-3 and HA were co-vapor deposited in such a manner that the proportion of compound HA was 3 mass% so as to cover the transparent electrode, to form a first hole transporting layer having a film thickness of 10 nm.

[0389] Compound HT-3 was vapor deposited on the first hole transporting layer to form a second hole transporting layer having a film thickness of 80 nm.

[0390] Compound HT-4 was vapor deposited on the second hole transporting layer to form a third hole transporting layer having a film thickness of 5 nm.

[0391] On the 3rd hole-transporting layer, compound BH-2 (host material) and compound BD-2 (dopant material) were co-evaporated in a manner that the proportion of compound BD-1 reached 1 mass%, to form a light-emitting layer having a film thickness of 20 nm.

[0392] On the light-emitting layer, compound ET-2 was evaporated to form a 1st electron-transporting layer having a film thickness of 5 nm.

[0393] On the 1st electron-transporting layer, compound 1-4 and lithium quinolate (Liq) were co-evaporated in a manner that the proportion of Liq reached 50 mass%, to form a 2nd electron-transporting layer having a film thickness of 25 nm.

[0394] On the 2nd electron-transporting layer, metal Yb was evaporated to form an electron-injecting layer having a film thickness of 1 nm.

[0395] On the electron-injecting layer, metal Al was evaporated to form a cathode having a film thickness of 50 nm.

[0396] The element configuration of the organic EL element of Example 4 is briefly shown below.

[0397] ITO (130) / HT-3:HA (10:3%) / HT-3 (80) / HT-4 (5) / BH-2:BD-2 (20:1%) / ET-2 (5) / compound 1-4:Liq (25:50%) / Yb (1) / Al (50) The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses expressed in percentages indicate the proportion (mass%) of the latter compound in the layer.

[0398] Examples 5 to 6 In the formation of the 2nd electron-transporting layer, the compound shown in Table 2 was used instead of compound 1-4, and otherwise, an organic EL element was produced and evaluated by the same method as in Example 4. The results are shown in Table 2.

[0399] [Table 2] <Physical property evaluation of compounds> For the 1st component and the comparative compound, the GSP (Giant Surface Polarization) slope and the energy level of the lowest unoccupied orbital (LUMO) were measured by the following measurement method. The results are shown in Table 3.

[0400] ・GSP (Giant Surface Polarization) slope The GSP (Giant Surface Polarization) slope was obtained by measuring the film thickness dependence of the surface polarization.

[0401] The light shielding was performed in a manner not to irradiate light to the measurement object in the chamber, and the surface potential of the measurement object was measured in a vacuum of 10 -5 The surface potential of the measurement object was measured in a vacuum of 10 Pa at a deposition rate of 2 A / s on an ITO substrate, and the surface potential (unit: mV) of the deposited film was measured. This was repeated 5 times, the vertical axis was set as the surface potential (unit: mV), the horizontal axis was set as the film thickness (unit: nm), each dot was fitted as a straight line by the least squares method, the value of the slope of the graph obtained from the dot was calculated, and was set as GSP_slope (unit: mV / nm). The measurement of the surface potential in a vacuum used a Kelvin probe device (manufactured by Tokyo Instruments Inc., "Ultra-high vacuum Kelvin probe").

[0402] It should be noted that both the deposition and the surface potential measurement were performed in a light-shielded and vacuum state. In addition, the sample was placed in the same chamber (light-shielded and vacuum) throughout the process of repeating the deposition and the measurement. "Repeated 5 times" means that 20 nm was deposited on the sample (ITO substrate) and the surface potential was measured, 20 nm was additionally deposited on the same sample (i.e., the thickness of the deposited film was a total of 40 nm) and the surface potential was measured, 20 nm was additionally deposited on the same sample (i.e., the thickness of the deposited film was a total of 60 nm) and the surface potential was measured, 20 nm was additionally deposited on the same sample (i.e., the thickness of the deposited film was a total of 80 nm) and the surface potential was measured, and 20 nm was additionally deposited on the same sample (i.e., the thickness of the deposited film was a total of 100 nm) and the surface potential was measured. (Reference) Y. Noguchi, Y. Miyazaki, Y. Tanaka, N. Sato, Y. Nakayama, T. D. Schmidt, W. Brutting, H. Ishii, Charge accumulation at organic semiconductor interfaces due to a permanent dipole moment and its orientational order in bilayer devices. J. Appl. Phys. 111, 114508 (2012). ・Energy level of the lowest unoccupied orbital (LUMO) The energy level of the lowest unoccupied orbital (LUMO: Lowest Unoccupied Molecular Orbital) was calculated using differential pulse voltammetry by the following mathematical expression (Equation 1Y) (unit: eV).

[0403] LUMO = -1.19 x (Ere - Efc) - 4.78 eV (Equation 1Y) In mathematical expression (num. 1Y), Ereand Efc are as described below.

[0404] Ere: First reduction potential of the measurement target (DPV, Negative scan) Efc: First oxidation potential of ferrocene (DPV, Positive scan), (ca. +0.55 V vs Ag / AgCl) The redox potential was measured by differential pulse voltammetry (DPV) using an electrochemical analyzer (CHI 852D, manufactured by ALS Co.). The sample solution used in the measurement was prepared by dissolving the measurement target in N,N-dimethylformamide (DMF) as a solvent so that the concentration thereof was 1.0 mmol / L, and dissolving tetrabutylammonium hexafluorophosphate (TBHP) as a supporting electrolyte so that the concentration thereof was 100 mmol / L.

[0405] As a working electrode, a glassy carbon electrode was used. As a counter electrode, a platinum (Pt) electrode was used. (Reference Literature) M. E. Thompson, et. al., Organic Electronics, 6 (2005), p. 11-20, Organic Electronics, 10 (2009), p. 515-520.

[0406] <Structure Condition of Compound> For the 1st component and the comparative example compound, whether or not the structure condition "not containing the structure represented by formula (M1) to formula (M4) in the molecule" is satisfied is shown in Table 3, [Compound 66] .

[0407] Example 7 An organic EL element was produced and evaluated by the same method as in Example 1. The results are shown in Table 3.

[0408] Example 8 In the formation of the 2nd electron transport layer, instead of Compound 1-1, Compound 1-2 was used, and otherwise, an organic EL element was produced and evaluated by the same method as in Example 7. The results are shown in Table 3.

[0409] Comparative Examples 6 to 10 In the formation of the 2nd electron transport layer, instead of Compound 1-1, the compound shown in Table 3 was used, and otherwise, an organic EL element was produced and evaluated by the same method as in Example 7. The results are shown in Table 3.

[0410] [Table 3] As is apparent from Table 3, the 2nd organic EL device of the present application (Examples 3 and 4) using a compound having GSP_slope and LUMO within the prescribed range and satisfying the specific structural condition has a low driving voltage and a high EQE ratio, and the EQE is also maintained at a low current density (0.1 mA / cm 2 ).

[0411] Ref 1-1 has GSP_slope and LUMO within the prescribed range, but does not satisfy the above-described structural condition (contains a structure represented by formula (Ml) within the molecule). As is apparent from Comparative Example 6 using Ref 1-1, the EQE ratio is low, and the EQE decreases at a low current density.

[0412] Ref 1-2 and Ref 1-3 have LUMO within the prescribed range and satisfy the above-described structural condition, but GSP_slope is outside the prescribed range. As is apparent from Comparative Examples 7 and 8 using these compounds, since LUMO is within the prescribed range, the voltage is the same as that of Examples 7 and 8, but the EQE ratio is low, and the EQE decreases at a low current density.

[0413] Ref 1-5 has GSP_slope within the prescribed range, but LUMO is outside the prescribed range, and does not satisfy the above-described structural condition (contains a structure represented by formula (M3) within the molecule). Ref 1-6 has GSP_slope within the prescribed range, LUMO is outside the prescribed range, and does not satisfy the above-described structural condition (contains a structure represented by formula (Ml) within the molecule). As is apparent from Comparative Examples 9 and 10 using these compounds, since LUMO is outside the prescribed range, the driving voltage is very high, and in addition, the EQE ratio is low, and the EQE decreases at a low current density.

[0414] < Synthesis of Compounds > (Synthesis Example 1) Synthesis of Compound 1-3 Compound 1-3 was synthesized by the following synthesis route.

[0415] [Compound 67] (1) Synthesis of Intermediate 2 To intermediate 1 (36.3 g), bis(pinacolato)diboron (55.2 g) and potassium acetate (32.0 g) was added NMP (360 mL) and bubbled for 30 minutes under nitrogen at 105°C. PCy3 (2.4 g) and Pd2(dba)3 (4.0 g) were added and stirred under nitrogen at 105°C for 2.5 hours. After the reaction solution was cooled to room temperature, celite filtration was performed and washed with ethyl acetate. The filtrate was washed with water three times and the organic phase was concentrated. The obtained residue was subjected to column chromatography to obtain intermediate 2 (34.7 g, yield 75%) as a white solid. [Chemical Formula 68] .

[0416] (2) Synthesis of compound 1-3 To intermediate 3 (9.2 g), Pd(PPh3)4 (0.5 g) and Aliquat 336 (0.9 g) was added toluene (180 mL) and 2M aqueous potassium carbonate solution (22 mL) and bubbled for 30 minutes under nitrogen. It was heated and stirred for 19 hours at 85°C after the addition of intermediate 2 (8.9 g). After the reaction solution was cooled to room temperature, water was added and the precipitated solid was filtered. The obtained crude product was purified by silica gel column chromatography and recrystallized with toluene to obtain compound 1-3 as a white solid (6.3 g, yield 46%).

[0417] The result of mass spectrometric analysis was m / e = 628 with respect to the molecular weight of 627.80, which was identified as compound 1-3 of the object.

[0418] The above detailed several embodiments and / or examples of the present application, but those skilled in the art can easily apply many changes to these as exemplified embodiments and / or examples, without departing substantially from the novel teachings and effects of the present application. Therefore, these many changes are also included in the scope of the present application.

[0419] The documents described in this specification and the contents of the application based on the Paris Convention priority of the present application are all cited.

Claims

1. An organic electroluminescent element comprising: cathode 、 Anode, and One or more organic layers disposed between the cathode and the anode; At least one of the one or more organic layers contains a first component and a second component, The first component is a compound represented by the following formula (1): The second component is selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, organometallic complexes containing alkali metals, organometallic complexes containing alkaline earth metals, and organometallic complexes containing rare earth metals; [Chemistry 69] In formula (1), R1~R 10 At least one of them is a group represented by formula (1A); R1 to R2 that are not the group represented by the formula (1A) 10 are each independently a hydrogen atom or a substituent A; Among them, R1~R 10 At least three of them are independently a group represented by formula (1A), a substituent A or a hydrogen atom serving as a deuterium atom; In formula (1A), L 1A for: single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; n1A is an integer from 0 to 3; When n1A is 0, (L 1A ) n1A is a single bond; When n1A is 2 or 3, multiple L 1A Connected in series, the structure in brackets is the farthest L from the anthracene skeleton. 1A Bonding; multiple L 1A Can be the same or different; X 11A C (R 21A )(R 22A )、N(R 23A ), O or S; By R 11A ~R 18A One or more adjacent two or more of them are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or do not form such a ring; When forming the substituted or unsubstituted monocyclic ring, one of the atoms constituting the monocyclic ring and L 1A R that is bonded to or does not participate in the formation of the monocyclic ring 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A Key; When forming the substituted or unsubstituted fused ring, one of the atoms constituting the fused ring and L 1A R that is bonded to or does not participate in the formation of the fused ring 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A Keys; When the monocyclic ring and condensed ring are not formed, R 11A ~R 18A and R 21A ~R 23A 1 in the expression is consistent with L 1A Key; Not indicated with the L 1A The bond does not form the ring R 11A ~R 18A and R 21A ~R 23A are each independently a hydrogen atom or a substituent A; When there are two or more groups represented by formula (1A), the two or more groups represented by formula (1A) may be the same as or different from each other; The substituent A is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 Each independently is: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; When there are two or more substituents A, the two or more substituents A may be the same or different from each other; R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same as or different from each other; The compound represented by formula (1) does not contain the structure represented by formula (M1), the structure represented by formula (M2), the structure represented by formula (M3), and the structure represented by formula (M4) in the molecule; [Chemistry 70] 。 2. The organic electroluminescent element according to claim 1, wherein R1~R 10 At least three of them are independently a group or substituent A represented by the formula (1A).

3. The organic electroluminescent element according to claim 1 or 2, wherein R1~R 10 Two of them are independently a substituent A, and the other R1 to R 10 One of them is a group represented by the above formula (1A).

4. The organic electroluminescent element according to any one of claims 1 to 3, wherein R9 and R 10 Each is independently a group or substituent A represented by the above formula (1A).

5. The organic electroluminescent element according to any one of claims 1 to 4, wherein R9 and R 10 One of the groups represented by formula (1A), R9 and R 10 The other is a substituent A.

6. The organic electroluminescent element according to claim 1 or 2, wherein R2, R9 and R 10 Each is independently a group or substituent A represented by the above formula (1A).

7. The organic electroluminescent element according to claim 6, wherein R9 and R 10 One of the groups represented by formula (1A), R9 and R 10 The other of R and R2 are each independently a substituent A.

8. The organic electroluminescent element according to any one of claims 1 to 7, wherein The group represented by the formula (1A) is a group represented by any one of the following formulas (1A-1) to (1A-3), [Chemistry 71] In formulas (1A-1) to (1A-3), L 1A and n1A are defined as in formula (1); X 11A C (R 21A )(R 22A )、N(R 23A ), O or S; R 21A ~R 23A 、R 111A ~R 120A 、R 121A ~R 130A and R 131A ~R 140A 1 in the expression is consistent with L 1A Keys; Not indicated with the L 1A The key R 21A ~R 23A 、R 111A ~R 120A 、R 121A ~R 130A and R 131A ~R 140A are each independently a hydrogen atom or a substituent A; The substituent A is as defined in formula (1).

9. The organic electroluminescent element according to any one of claims 1 to 8, wherein X 11A O or S.

10. The organic electroluminescent element according to claim 1, wherein The compound represented by the formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3), [Chemistry 72] In formulas (1-1) to (1-3), L 1A and n1A are defined as in formula (1), X 111A O or S; R 12 and R 19 are each independently a substituent A; R 11 、R 13 ~R 18 、R 121A ~R 140A are each independently a hydrogen atom or a substituent A; The substituent A is as defined in formula (1); The compound represented by any one of the formulae (1-1) to (1-3) does not contain the structure represented by the following formula (M1), the structure represented by the following formula (M2), the structure represented by the following formula (M3), and the structure represented by the following formula (M4) in the molecule; [Chemistry 73] 。 11. The organic electroluminescent element according to any one of claims 1 to 10, wherein L 1A For a single bond.

12. The organic electroluminescent element according to claim 1, wherein The compound represented by the formula (1) is a compound represented by any one of the following formulas (1-11) to (1-41), [Chemistry 74] In formulas (1-11) to (1-41), X 111A O or S; R 12 、R 13 and R 19 are each independently a substituent A; R 121A ~R 140A are each independently a hydrogen atom or a substituent A; The substituent A is as defined in formula (1); The compound represented by any one of the formulae (1-11) to (1-41) does not contain the structure represented by the following formula (M1), the structure represented by the following formula (M2), the structure represented by the following formula (M3), and the structure represented by the following formula (M4) in the molecule; [Chemistry 75] 。 13. An organic electroluminescent element comprising: cathode, Anode, and One or more organic layers disposed between the cathode and the anode; At least one of the one or more organic layers contains a first component and a second component, The first component is a compound that satisfies the following formula (R1) and formula (R2), and does not contain the structures represented by the following formulas (M1) to (M4) in the molecule. The second component is selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, organometallic complexes containing alkali metals, organometallic complexes containing alkaline earth metals, and organometallic complexes containing rare earth metals; 40mV / nm≤GSP_slope・・・(R1) -2.80eV<LUMO<-1.86eV・・・(R2) [Chemistry 76] In formula (R1), GSP_slope represents the giant surface potential gradient; in formula (R2), LUMO represents the energy level of the lowest unoccupied orbital.

14. The organic electroluminescent element according to claim 13, wherein The first component satisfies the following formula (R1-1): GSP_slope≤60mV / nm・・・(R1-1) In formula (R1-1), GSP_slope is defined as in formula (R1).

15. The organic electroluminescent element according to claim 13 or 14, wherein The first component satisfies the following formula (R1-2): 41mV / nm≤GSP_slope・・・(R1-2) In formula (R1-2), GSP_slope is defined as in formula (R1).

16. The organic electroluminescent element according to claim 13, wherein The first component satisfies the following formula (R1-3): 41mV / nm≤GSP_slope≤60mV / nm・・・(R1-3) In formula (R1-3), GSP_slope is defined as in formula (R1).

17. The organic electroluminescent element according to claim 13, wherein The first component satisfies the following formula (R1-4): 42mV / nm≤GSP_slope≤51mV / nm・・・(R1-4) In formula (R1-4), GSP_slope is defined as in formula (R1).

18. The organic electroluminescent element according to any one of claims 13 to 17, wherein The first component satisfies the following formula (R2-1): -2.60eV≤LUMO≤-2.00eV・・・(R2-1) In formula (R2-1), LUMO is as defined in formula (R2).

19. The organic electroluminescent element according to any one of claims 13 to 17, wherein The first component satisfies the following formula (R2-2): -2.26eV≤LUMO≤-2.09eV・・・(R2-2) In formula (R2-2), LUMO is as defined in formula (R2).

20. The organic electroluminescent element according to claim 13, wherein The first component satisfies the following formula (R1-3) and the following formula (R2-2), 41mV / nm≤GSP_slope≤60mV / nm・・・(R1-3) -2.26eV≤LUMO≤-2.09eV・・・(R2-2) In formula (R1-3), GSP_slope is as defined in formula (R1), and in formula (R2-2), LUMO is as defined in formula (R2).

21. The organic electroluminescent element according to any one of claims 1 to 20, wherein The second component is selected from alkali metals, alkali metal compounds, and organic metal complexes containing alkali metals.

22. The organic electroluminescent element according to any one of claims 1 to 21, wherein The ratio of the first component to the total of the first component and the second component is 30 to 70% by mass.

23. The organic electroluminescent element according to any one of claims 1 to 22, wherein The device comprises an anode, a light-emitting layer, an electron-transporting region, and a cathode in this order, wherein at least one layer of the electron-transporting region comprises the first component and the second component.

24. The organic electroluminescent element according to claim 23, wherein The electron transport region includes at least a first layer and a second layer in order from the light emitting layer side, The second layer includes the first component and the second component.

25. The organic electroluminescent element according to claim 24, wherein The second layer substantially contains only the first component and the second component. 26 . An electronic device comprising the organic electroluminescent element according to claim 1 .

27. A compound represented by the following formula (2), [Chemistry 77] In formula (2), Ring a is: a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 6 to 50 ring atoms; R 101 ~R 107 、R 111 ~R 113 、R 121 ~R 125 and R 131 ~R 135 are each independently a hydrogen atom or a substituent R; in, R 111 ~R 113 At least one of them is a substituent R, or the ring a has at least one substituent; The substituent R is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 Each independently is: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Can be the same or different; When there are two or more substituents R, the two or more substituents R may be the same or different.

28. The compound according to claim 27, wherein The compound represented by the formula (2) is a compound represented by the following formula (2-1), [Chemistry 78] In formula (2-1), R 101 ~R 107 、R 111 ~R 119 、R 121 ~R 125 and R 131 ~R 135 are each independently a hydrogen atom or a substituent R; Among them, R 111 ~R 119 At least one of them is a substituent R; The substituent R is as defined in formula (2).

29. The compound according to claim 27, wherein The compound represented by the formula (2) is a compound represented by the following formula (2-11), [Chemistry 79] In formula (2-11), R 101 ~R 107 、R 111 ~R 115 、R 117 ~R 119 、R 121 ~R 125 、R 131 ~R 135 and R 141 ~R 145 are each independently a hydrogen atom or a substituent R; The substituent R is as defined in formula (2).

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